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45205008<section>Experiments</section><author><username>plus.google.com-+KatrinaBadiola</username><name>Katrina Badiola</name></author><content><![CDATA[[i]PS = Pictet-Spengler[/i] ======================================= TO DO: - Remove grease from final sample - H-NMR both samples - KAB8-14 has been concluded. Still finalising KAB1-5. ======================================= ***Experiment still in progress with regular updates. Last updated 12/03/12. START: 21/02/12 FINISH: [b][u]Background[/b][/u] <img src="http://www.ourexperiment.org/data/files/3238/Scheme%20KAB8-14.png" width="550"/> <img src="http://www.ourexperiment.org/data/files/3240/Table%20KAB8-14.jpg" width="550"/> [b][u]Hazard and Risk Assessment[/b][/u] As for KAB8-11 and KAB1-3. [data]3007[/data][data]3027[/data] [b][u]Previous Related Experiments[/b][/u] [blog]4510[/blog] [blog]4376[/blog] [blog]4380[/blog] [b][u]Following Experiments[/b][/u] [blog]4540[/blog] [blog]4684[/blog] [blog]4755[/blog] [b][u]Procedure[/b][/u] [b]21/02/12[/b] [b]General procedure.[/b] The peptide acetal Ugi-intermediate was dissolved in toluene before the addition of triflic acid at rt. The reaction vessel was immediately fitted with a condensing tube and placed in a pre-heated oil bath at 90 °C. The reaction mixture was reflux heated and the progress monitored by TLC against the relevant starting material and the expected product. [b]KAB8-14.[/b] Peptide acetal MNR10-2 (302.4 mg, 0.659 mmol), toluene (30 mL), TfOH (2.92 μL, 0.033 mmol, 5 mol%). [b]KAB1-5.[/b] Peptide acetal MNR8-3 (381.6 mg, 0.821 mmol), toluene (38 mL), TfOH (3.64 μL, 0.041 mmol, 5 mol%). [data]3247[/data][data]3253[/data][data]3259[/data][data]3265[/data][data]3271[/data] [b]Monitoring the Reaction Progress by TLC[/b] All TLCs were eluted with EtOAc/hexane, 5:3, v/v and stained with KMnO<sub>4</sub>. Time noted is the amount elapsed since the addition of acid. [data]3243[/data][data]3245[/data][data]3249[/data][data]3251[/data][data]3255[/data] [data]3257[/data][data]3261[/data][data]3263[/data][data]3267[/data][data]3269[/data] [data]3273[/data][data]3275[/data] [b]Workup Procedure[/b] After 3.5 hours the reaction mixture was allowed to cool. After the mixture was diluted with EtOAc (50 mL) then quenched with saturated sodium bicarbonate solution (50 mL), the organic layer was separated. The aqueous fraction was extracted with EtOAc (3 × 30 mL) before the organic layers were combined then dried over magnesium sulfate and filtered. The pale yellow KAB8-14 and the yellow KAB1-5 solutions were concentrated under reduced pressure to give the crude products. KAB8-14 as a orangish semi-solid (249.8 mg, 103%) and KAB1-5 as a reddish semi-solid (312.0 mg, 102%). [data]3277[/data][data]3297[/data] [b]Purification[/b] Both crude KAB8-14 and KAB1-5 residues were dissolved in EtOAc. The solutions were passed through silica pads then concentrated under reduced pressure. KAB8-14 (233 mg, 96%). KAB1-5 (279 mg, 91%). [data]3353[/data][data]3355[/data] Recrystallisation from EtOAc/hexane. KAB8-14 Start: 226 mg Pure KAB8-14: 211 mg (93%). 07/02/12 - Attempt at reXST of KAB1-5 from EtOAc/Et<sub>2</sub>O [b][u]Summary and Conclusion[/b][/u] ----------------------------------------------------------------------------- NOTES 21/02/12 - KAB8-14 Flask: 49.1531 g - Forgot to weigh out KAB1-5 flask. Will weigh it out after the filtration step tomorrow. NOTES 28/02/12 - Still testing a recrystallisation of crude KAB1-2 before any attempting with the KAB1-5 sample. - KAB8-13 filter paper: 1.1914 g NOTES 29/02/12 - Still attempting to recrystallise an old sample of KAB1-2. Unsuccessful so far. No attempt at the recrystallisation of KAB1-5 as of yet. -----------------------------------------------------------------------------]]></content><html><![CDATA[<i>PS = Pictet-Spengler</i><br style="clear:left;"/><br style="clear:left;"/>=======================================<br style="clear:left;"/>TO DO: <br style="clear:left;"/>- Remove grease from final sample<br style="clear:left;"/>- H-NMR both samples<br style="clear:left;"/>- KAB8-14 has been concluded. Still finalising KAB1-5.<br style="clear:left;"/>=======================================<br style="clear:left;"/><br style="clear:left;"/>***Experiment still in progress with regular updates. Last updated 12/03/12.<br style="clear:left;"/><br style="clear:left;"/>START: 21/02/12<br style="clear:left;"/>FINISH: <br style="clear:left;"/><br style="clear:left;"/><b><u>Background</b></u><br style="clear:left;"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/3238/Scheme%20KAB8-14.png" width="550"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/3240/Table%20KAB8-14.jpg" width="550"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Hazard and Risk Assessment</b></u><br style="clear:left;"/>As for KAB8-11 and KAB1-3.<br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3007.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3007&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Hazard and Risk Assessment KAB8-11</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3027.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3027&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Hazard and Risk Assessment KAB1-3</div></div><br style="clear:left;"/><br style="clear:left;"/><b><u>Previous Related Experiments</b></u><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4510/AgCl_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB813.html">AgCl catalysed PS to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-13)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4376/The_TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB812.html">The TfOH catalysed PS* reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-12)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4380/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB14.html">TfOH catalysed PS* reaction to give the dimethoxy PZQ analogue (KAB1-4)</a><br style="clear:left;"/><br style="clear:left;"/><b><u>Following Experiments</b></u><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4540/TfOH_catalysed_partial_PS_reactions_to_give_the_enediamide_intermediates_of_PZQ_and_the_Nbenzoyl_analogue_KAB132__KAB171.html">TfOH catalysed partial PS* reactions to give the enediamide intermediates of PZQ and the <i>N</i>-benzoyl analogue (KAB13-2 & KAB17-1)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4684/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB815.html">AgOTf catalysed PS reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-15)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4755/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB16.html">AgOTf catalysed PS reaction to give the dimethoxy PZQ analogue (KAB1-6)</a><br style="clear:left;"/><br style="clear:left;"/><b><u>Procedure</b></u><br style="clear:left;"/><br style="clear:left;"/><b>21/02/12</b><br style="clear:left;"/><b>General procedure.</b> The peptide acetal Ugi-intermediate was dissolved in toluene before the addition of triflic acid at rt. The reaction vessel was immediately fitted with a condensing tube and placed in a pre-heated oil bath at 90 °C. The reaction mixture was reflux heated and the progress monitored by TLC against the relevant starting material and the expected product.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-14.</b> Peptide acetal MNR10-2 (302.4 mg, 0.659 mmol), toluene (30 mL), TfOH (2.92 μL, 0.033 mmol, 5 mol%).<br style="clear:left;"/><br style="clear:left;"/><b>KAB1-5.</b> Peptide acetal MNR8-3 (381.6 mg, 0.821 mmol), toluene (38 mL), TfOH (3.64 μL, 0.041 mmol, 5 mol%).<br style="clear:left;"/><br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3247.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3247&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (5 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3253.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3253&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (15 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3259.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3259&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (30 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3265.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3265&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (1 h)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3271.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3271&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (3 h)</div></div><br style="clear:left;"/><br style="clear:left;"/><b>Monitoring the Reaction Progress by TLC</b><br style="clear:left;"/>All TLCs were eluted with EtOAc/hexane, 5:3, v/v and stained with KMnO<sub>4</sub>. Time noted is the amount elapsed since the addition of acid.<br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3243.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3243&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (5 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3245.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3245&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (5 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3249.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3249&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (15 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3251.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3251&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (15 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3255.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3255&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (30 min)</div></div><br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3257.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3257&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (30 min)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3261.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3261&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (1 h)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3263.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3263&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (1 h)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3267.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3267&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (2 h)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3269.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3269&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (2 h)</div></div><br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3273.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3273&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (3 h)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3275.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3275&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (3 h)</div></div><br style="clear:left;"/><br style="clear:left;"/><b>Workup Procedure</b><br style="clear:left;"/>After 3.5 hours the reaction mixture was allowed to cool. After the mixture was diluted with EtOAc (50 mL) then quenched with saturated sodium bicarbonate solution (50 mL), the organic layer was separated. The aqueous fraction was extracted with EtOAc (3 × 30 mL) before the organic layers were combined then dried over magnesium sulfate and filtered. <br style="clear:left;"/>The pale yellow KAB8-14 and the yellow KAB1-5 solutions were concentrated under reduced pressure to give the crude products. KAB8-14 as a orangish semi-solid (249.8 mg, 103%) and KAB1-5 as a reddish semi-solid (312.0 mg, 102%).<br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3277.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3277&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Crude KAB8-14</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3297.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3297&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Crude KAB1-5</div></div><br style="clear:left;"/><br style="clear:left;"/><b>Purification</b><br style="clear:left;"/>Both crude KAB8-14 and KAB1-5 residues were dissolved in EtOAc. The solutions were passed through silica pads then concentrated under reduced pressure. <br style="clear:left;"/>KAB8-14 (233 mg, 96%).<br style="clear:left;"/>KAB1-5 (279 mg, 91%).<br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3353.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3353&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Filtered KAB8-14</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3355.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3355&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Filtered KAB1-5</div></div><br style="clear:left;"/><br style="clear:left;"/>Recrystallisation from EtOAc/hexane.<br style="clear:left;"/>KAB8-14 Start: 226 mg<br style="clear:left;"/>Pure KAB8-14: 211 mg (93%).<br style="clear:left;"/><br style="clear:left;"/>07/02/12 - Attempt at reXST of KAB1-5 from EtOAc/Et<sub>2</sub>O<br style="clear:left;"/><br style="clear:left;"/><b><u>Summary and Conclusion</b></u><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>-----------------------------------------------------------------------------<br style="clear:left;"/>NOTES 21/02/12<br style="clear:left;"/>- KAB8-14 Flask: 49.1531 g<br style="clear:left;"/>- Forgot to weigh out KAB1-5 flask. Will weigh it out after the filtration step tomorrow.<br style="clear:left;"/><br style="clear:left;"/>NOTES 28/02/12<br style="clear:left;"/>- Still testing a recrystallisation of crude KAB1-2 before any attempting with the KAB1-5 sample.<br style="clear:left;"/>- KAB8-13 filter paper: 1.1914 g<br style="clear:left;"/><br style="clear:left;"/>NOTES 29/02/12<br style="clear:left;"/>- Still attempting to recrystallise an old sample of KAB1-2. Unsuccessful so far. No attempt at the recrystallisation of KAB1-5 as of yet.<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>-----------------------------------------------------------------------------<div class="postTools"><div class="postLinkedBut" onclick="$('#postLinked_4520').fadeIn();">Linked Posts</div></div> <div class="postLinkedItems" id="postLinked_4520"><b>This post is linked by:</b><ul> <li><a href="http://www.ourexperiment.org/racemic_pzq/4376/The_TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB812.html">The TfOH catalysed PS* reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-12)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4441/TfOH_catalysed_PS_reaction_to_give_the_Nbenzoyl_PZQ_analogue_KAB73.html">TfOH catalysed PS* reaction to give the <i>N</i>-benzoyl PZQ analogue (KAB7-3)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/3936/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB89.html">TfOH catalysed PS* reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-9)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4344/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB13.html">TfOH catalysed PS* reaction to give the dimethoxy PZQ analogue (KAB1-3)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4323/The_TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB811.html">The TfOH catalysed PS* reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-11)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4856/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB816.html">AgOTf catalysed PS reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-16)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4510/AgCl_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB813.html">AgCl catalysed PS to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-13)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4755/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB16.html">AgOTf catalysed PS reaction to give the dimethoxy PZQ analogue (KAB1-6)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4380/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB14.html">TfOH catalysed PS* reaction to give the dimethoxy PZQ analogue (KAB1-4)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4540/TfOH_catalysed_partial_PS_reactions_to_give_the_enediamide_intermediates_of_PZQ_and_the_Nbenzoyl_analogue_KAB132__KAB171.html">TfOH catalysed partial PS* reactions to give the enediamide intermediates of PZQ and the <i>N</i>-benzoyl analogue (KAB13-2 & KAB17-1)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4248/KAB_ExperimentCompound_Index.html">KAB Experiment/Compound Index</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4453/TfOH_catalysed_PS_reaction_to_give_PZQ_KAB317.html">TfOH catalysed PS* reaction to give PZQ (KAB3-17)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/6441/mnr12X__duplicate_post_of_KAB814.html">mnr12-X - duplicate post of KAB8-14</a></li></ul></div> ]]></html><datestamp>2012-02-21T02:16:31+00:00</datestamp><timestamp>2012-03-12T10:43:26+00:00</timestamp><blog>6</blog><key>89284bf33196bfb5a1c31a0e45639c34</key><attached_data><data>https://www.ourexperiment.org/data/3239.xml</data><data>https://www.ourexperiment.org/data/3241.xml</data><data>https://www.ourexperiment.org/data/3243.xml</data><data>https://www.ourexperiment.org/data/3245.xml</data><data>https://www.ourexperiment.org/data/3247.xml</data><data>https://www.ourexperiment.org/data/3249.xml</data><data>https://www.ourexperiment.org/data/3251.xml</data><data>https://www.ourexperiment.org/data/3253.xml</data><data>https://www.ourexperiment.org/data/3255.xml</data><data>https://www.ourexperiment.org/data/3257.xml</data><data>https://www.ourexperiment.org/data/3259.xml</data><data>https://www.ourexperiment.org/data/3261.xml</data><data>https://www.ourexperiment.org/data/3263.xml</data><data>https://www.ourexperiment.org/data/3265.xml</data><data>https://www.ourexperiment.org/data/3267.xml</data><data>https://www.ourexperiment.org/data/3269.xml</data><data>https://www.ourexperiment.org/data/3271.xml</data><data>https://www.ourexperiment.org/data/3273.xml</data><data>https://www.ourexperiment.org/data/3275.xml</data><data>https://www.ourexperiment.org/data/3277.xml</data><data>https://www.ourexperiment.org/data/3297.xml</data><data>https://www.ourexperiment.org/data/3353.xml</data><data>https://www.ourexperiment.org/data/3355.xml</data></attached_data><links><uri>http://www.ourexperiment.org/uri/1f4</uri><permalink>https://www.ourexperiment.org/racemic_pzq/4520/TfOH_catalysed_PS_reactions_to_give_the_dimethoxy_PZQ_analogues_KAB814__KAB15.html</permalink></links><formats><format 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current="true">https://www.ourexperiment.org/racemic_pzq/4520/TfOH_catalysed_PS_reactions_to_give_the_dimethoxy_PZQ_analogues_KAB814__KAB15.xml?revision=5008</revision><revision>https://www.ourexperiment.org/racemic_pzq/4520/TfOH_catalysed_PS_reactions_to_give_the_dimethoxy_PZQ_analogues_KAB814__KAB15.xml?revision=6997</revision></revisions><comments/></post><post><id>4520</id><rid>6997</rid><title/><section>Experiments</section><author><username>plus.google.com-+KatrinaBadiola</username><name>Katrina Badiola</name></author><content><![CDATA[[i]PS = Pictet-Spengler[/i] ======================================= TO DO: - Remove grease from final sample - H-NMR both samples - KAB8-14 has been concluded. Still finalising KAB1-5. ======================================= ***Experiment still in progress with regular updates. Last updated 12/03/12. START: 21/02/12 FINISH: [b][u]Background[/b][/u] <img src="http://www.ourexperiment.org/data/files/3238/Scheme%20KAB8-14.png" width="550"/> <img src="http://www.ourexperiment.org/data/files/3240/Table%20KAB8-14.jpg" width="550"/> [b][u]Hazard and Risk Assessment[/b][/u] As for KAB8-11 and KAB1-3. [data]3007[/data][data]3027[/data] [b][u]Previous Related Experiments[/b][/u] [blog]4510[/blog] [blog]4376[/blog] [blog]4380[/blog] [b][u]Following Experiments[/b][/u] [blog]4540[/blog] [blog]4684[/blog] [blog]4755[/blog] [b][u]Procedure[/b][/u] [b]21/02/12[/b] [b]General procedure.[/b] The peptide acetal Ugi-intermediate was dissolved in toluene before the addition of triflic acid at rt. The reaction vessel was immediately fitted with a condensing tube and placed in a pre-heated oil bath at 90 °C. The reaction mixture was reflux heated and the progress monitored by TLC against the relevant starting material and the expected product. [b]KAB8-14.[/b] Peptide acetal MNR10-2 (302.4 mg, 0.659 mmol), toluene (30 mL), TfOH (2.92 μL, 0.033 mmol, 5 mol%). [b]KAB1-5.[/b] Peptide acetal MNR8-3 (381.6 mg, 0.821 mmol), toluene (38 mL), TfOH (3.64 μL, 0.041 mmol, 5 mol%). [data]3247[/data][data]3253[/data][data]3259[/data][data]3265[/data][data]3271[/data] [b]Monitoring the Reaction Progress by TLC[/b] All TLCs were eluted with EtOAc/hexane, 5:3, v/v and stained with KMnO<sub>4</sub>. Time noted is the amount elapsed since the addition of acid. [data]3243[/data][data]3245[/data][data]3249[/data][data]3251[/data][data]3255[/data] [data]3257[/data][data]3261[/data][data]3263[/data][data]3267[/data][data]3269[/data] [data]3273[/data][data]3275[/data] [b]Workup Procedure[/b] After 3.5 hours the reaction mixture was allowed to cool. After the mixture was diluted with EtOAc (50 mL) then quenched with saturated sodium bicarbonate solution (50 mL), the organic layer was separated. The aqueous fraction was extracted with EtOAc (3 × 30 mL) before the organic layers were combined then dried over magnesium sulfate and filtered. The pale yellow KAB8-14 and the yellow KAB1-5 solutions were concentrated under reduced pressure to give the crude products. KAB8-14 as a orangish semi-solid (249.8 mg, 103%) and KAB1-5 as a reddish semi-solid (312.0 mg, 102%). [data]3277[/data][data]3297[/data] [b]Purification[/b] Both crude KAB8-14 and KAB1-5 residues were dissolved in EtOAc. The solutions were passed through silica pads then concentrated under reduced pressure. KAB8-14 (233 mg, 96%). KAB1-5 (279 mg, 91%). [data]3353[/data][data]3355[/data] Recrystallisation from EtOAc/hexane. KAB8-14 Start: 226 mg Pure KAB8-14: 211 mg (93%). 07/02/12 - Attempt at reXST of KAB1-5 from EtOAc/Et<sub>2</sub>O [b][u]Summary and Conclusion[/b][/u] ----------------------------------------------------------------------------- NOTES 21/02/12 - KAB8-14 Flask: 49.1531 g - Forgot to weigh out KAB1-5 flask. Will weigh it out after the filtration step tomorrow. NOTES 28/02/12 - Still testing a recrystallisation of crude KAB1-2 before any attempting with the KAB1-5 sample. - KAB8-13 filter paper: 1.1914 g NOTES 29/02/12 - Still attempting to recrystallise an old sample of KAB1-2. Unsuccessful so far. No attempt at the recrystallisation of KAB1-5 as of yet. -----------------------------------------------------------------------------]]></content><html><![CDATA[<i>PS = Pictet-Spengler</i><br style="clear:left;"/><br style="clear:left;"/>=======================================<br style="clear:left;"/>TO DO: <br style="clear:left;"/>- Remove grease from final sample<br style="clear:left;"/>- H-NMR both samples<br style="clear:left;"/>- KAB8-14 has been concluded. Still finalising KAB1-5.<br style="clear:left;"/>=======================================<br style="clear:left;"/><br style="clear:left;"/>***Experiment still in progress with regular updates. Last updated 12/03/12.<br style="clear:left;"/><br style="clear:left;"/>START: 21/02/12<br style="clear:left;"/>FINISH: <br style="clear:left;"/><br style="clear:left;"/><b><u>Background</b></u><br style="clear:left;"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/3238/Scheme%20KAB8-14.png" width="550"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/3240/Table%20KAB8-14.jpg" width="550"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Hazard and Risk Assessment</b></u><br style="clear:left;"/>As for KAB8-11 and KAB1-3.<br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3007.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3007&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Hazard and Risk Assessment KAB8-11</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3027.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3027&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Hazard and Risk Assessment KAB1-3</div><br style="clear:left;"/><br style="clear:left;"/><b><u>Previous Related Experiments</b></u><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4510/AgCl_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB813.html">AgCl catalysed PS to give the dimethoxy N-benzoyl PZQ analogue (KAB8-13)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4376/The_TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB812.html">The TfOH catalysed PS* reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-12)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4380/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB14.html">TfOH catalysed PS* reaction to give the dimethoxy PZQ analogue (KAB1-4)</a><br style="clear:left;"/><br style="clear:left;"/><b><u>Following Experiments</b></u><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4540/TfOH_catalysed_partial_PS_reactions_to_give_the_enediamide_intermediates_of_PZQ_and_the_Nbenzoyl_analogue_KAB132__KAB171.html">TfOH catalysed partial PS* reactions to give the enediamide intermediates of PZQ and the N-benzoyl analogue (KAB13-2 & KAB17-1)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4684/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB815.html">AgOTf catalysed PS reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-15)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/4755/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB16.html">AgOTf catalysed PS reaction to give the dimethoxy PZQ analogue (KAB1-6)</a><br style="clear:left;"/><br style="clear:left;"/><b><u>Procedure</b></u><br style="clear:left;"/><br style="clear:left;"/><b>21/02/12</b><br style="clear:left;"/><b>General procedure.</b> The peptide acetal Ugi-intermediate was dissolved in toluene before the addition of triflic acid at rt. The reaction vessel was immediately fitted with a condensing tube and placed in a pre-heated oil bath at 90 °C. The reaction mixture was reflux heated and the progress monitored by TLC against the relevant starting material and the expected product.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-14.</b> Peptide acetal MNR10-2 (302.4 mg, 0.659 mmol), toluene (30 mL), TfOH (2.92 μL, 0.033 mmol, 5 mol%).<br style="clear:left;"/><br style="clear:left;"/><b>KAB1-5.</b> Peptide acetal MNR8-3 (381.6 mg, 0.821 mmol), toluene (38 mL), TfOH (3.64 μL, 0.041 mmol, 5 mol%).<br style="clear:left;"/><br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3247.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3247&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (5 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3253.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3253&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (15 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3259.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3259&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (30 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3265.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3265&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (1 h)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3271.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3271&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Reaction mixtures (3 h)</div><br style="clear:left;"/><br style="clear:left;"/><b>Monitoring the Reaction Progress by TLC</b><br style="clear:left;"/>All TLCs were eluted with EtOAc/hexane, 5:3, v/v and stained with KMnO<sub>4</sub>. Time noted is the amount elapsed since the addition of acid.<br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3243.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3243&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (5 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3245.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3245&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (5 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3249.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3249&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (15 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3251.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3251&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (15 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3255.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3255&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (30 min)</div><br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3257.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3257&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (30 min)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3261.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3261&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (1 h)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3263.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3263&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (1 h)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3267.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3267&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (2 h)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3269.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3269&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (2 h)</div><br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3273.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3273&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-14 reaction mixture (3 h)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3275.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3275&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB1-5 reaction mixture (3 h)</div><br style="clear:left;"/><br style="clear:left;"/><b>Workup Procedure</b><br style="clear:left;"/>After 3.5 hours the reaction mixture was allowed to cool. After the mixture was diluted with EtOAc (50 mL) then quenched with saturated sodium bicarbonate solution (50 mL), the organic layer was separated. The aqueous fraction was extracted with EtOAc (3 × 30 mL) before the organic layers were combined then dried over magnesium sulfate and filtered. <br style="clear:left;"/>The pale yellow KAB8-14 and the yellow KAB1-5 solutions were concentrated under reduced pressure to give the crude products. KAB8-14 as a orangish semi-solid (249.8 mg, 103%) and KAB1-5 as a reddish semi-solid (312.0 mg, 102%).<br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3277.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3277&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Crude KAB8-14</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3297.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3297&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Crude KAB1-5</div><br style="clear:left;"/><br style="clear:left;"/><b>Purification</b><br style="clear:left;"/>Both crude KAB8-14 and KAB1-5 residues were dissolved in EtOAc. The solutions were passed through silica pads then concentrated under reduced pressure. <br style="clear:left;"/>KAB8-14 (233 mg, 96%).<br style="clear:left;"/>KAB1-5 (279 mg, 91%).<br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3353.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3353&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Filtered KAB8-14</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/3355.html','_blank','scrollbars=1;menubar=no,height=750,width=680,resizable=yes,toolbar=no,location=no,status=no');" style="width:100px; height:auto;"><div style="background-repeat: no-repeat; background-position: center center; background-image: url(/getdata.php?bit=3355&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Filtered KAB1-5</div><br style="clear:left;"/><br style="clear:left;"/>Recrystallisation from EtOAc/hexane.<br style="clear:left;"/>KAB8-14 Start: 226 mg<br style="clear:left;"/>Pure KAB8-14: 211 mg (93%).<br style="clear:left;"/><br style="clear:left;"/>07/02/12 - Attempt at reXST of KAB1-5 from EtOAc/Et<sub>2</sub>O<br style="clear:left;"/><br style="clear:left;"/><b><u>Summary and Conclusion</b></u><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>-----------------------------------------------------------------------------<br style="clear:left;"/>NOTES 21/02/12<br style="clear:left;"/>- KAB8-14 Flask: 49.1531 g<br style="clear:left;"/>- Forgot to weigh out KAB1-5 flask. Will weigh it out after the filtration step tomorrow.<br style="clear:left;"/><br style="clear:left;"/>NOTES 28/02/12<br style="clear:left;"/>- Still testing a recrystallisation of crude KAB1-2 before any attempting with the KAB1-5 sample.<br style="clear:left;"/>- KAB8-13 filter paper: 1.1914 g<br style="clear:left;"/><br style="clear:left;"/>NOTES 29/02/12<br style="clear:left;"/>- Still attempting to recrystallise an old sample of KAB1-2. Unsuccessful so far. No attempt at the recrystallisation of KAB1-5 as of yet.<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>-----------------------------------------------------------------------------<div class="postTools"><div class="postLinkedBut" onclick="$('#postLinked_4520').fadeIn();">Linked Entries</div></div> <div class="postLinkedItems" id="postLinked_4520"><b>This entry is linked by:</b><ul> <li><a href="http://www.ourexperiment.org/racemic_pzq/4376/The_TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB812.html">The TfOH catalysed PS* reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-12)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4441/TfOH_catalysed_PS_reaction_to_give_the_Nbenzoyl_PZQ_analogue_KAB73.html">TfOH catalysed PS* reaction to give the N-benzoyl PZQ analogue (KAB7-3)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/3936/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB89.html">TfOH catalysed PS* reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-9)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4344/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB13.html">TfOH catalysed PS* reaction to give the dimethoxy PZQ analogue (KAB1-3)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4323/The_TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB811.html">The TfOH catalysed PS* reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-11)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4856/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB816.html">AgOTf catalysed PS reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-16)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4510/AgCl_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB813.html">AgCl catalysed PS to give the dimethoxy N-benzoyl PZQ analogue (KAB8-13)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4755/AgOTf_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB16.html">AgOTf catalysed PS reaction to give the dimethoxy PZQ analogue (KAB1-6)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4380/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_PZQ_analogue_KAB14.html">TfOH catalysed PS* reaction to give the dimethoxy PZQ analogue (KAB1-4)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4540/TfOH_catalysed_partial_PS_reactions_to_give_the_enediamide_intermediates_of_PZQ_and_the_Nbenzoyl_analogue_KAB132__KAB171.html">TfOH catalysed partial PS* reactions to give the enediamide intermediates of PZQ and the N-benzoyl analogue (KAB13-2 & KAB17-1)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4248/KAB_ExperimentCompound_Index.html">KAB Experiment/Compound Index</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4453/TfOH_catalysed_PS_reaction_to_give_PZQ_KAB317.html">TfOH catalysed PS* reaction to give PZQ (KAB3-17)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/6441/mnr12X__duplicate_post_of_KAB814.html">mnr12-X - duplicate post of KAB8-14</a></li></ul></div> 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