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39124816<section>Experiments</section><author><username>plus.google.com-+KatrinaBadiola</username><name>Katrina Badiola</name></author><content><![CDATA[[i]*PS = Pictet-Spengler[/i] [b][u]Background[/b][/u] Repeat of procedure for the preparation of KAB8-5 with reduced catalyst loading. <img src="http://www.ourexperiment.org/data/files/2648/Scheme%20KAB8-7.png" width="550"/>[blog]3936[/blog] <img src="" width="400"/> [b][u]Hazard and Risk Assessment[/b][/u] As for KAB8-5 ([url=http://www.ourexperiment.org/data/files/2630/HRA%20KAB8-5.pdf]here[/url]) [b][u]Previous Related Experiments[/b][/u] [blog]3873[/blog] [blog]3660[/blog] [b][u]Following Experiments[/b][/u] [blog]3936[/blog] [b][u]Procedure[/b][/u] [b]Preparation of stock acid[/b]: A 0.26 M solution of TfOH in toluene was prepared by mixing TfOH (~195 mg, 1.3 mmol) in toluene (5 mL). It was assumed the TfOH contributed negligible volume. [b]KAB8-7[/b]: MNR10-1 (153.9 mg, 0.336 mmol) was dissolved in toluene (32 mL) before the TfOH/toluene mixture (0.39 mL; TfOH = 30 mol%) was added at 12:30 at rt. The mixture was heated to 90 °C. [b]KAB8-8[/b]: The procedure was the same as for KAB8-7. MNR10-1 (94.8 mg, 0.207 mmol), toluene (32 mL), TfOH/toluene (0.12 mL; TfOH = 15 mol%). Added at 12:35 at rt, before heated to 90 °C. Aliquot 1 (50 uL) extracted from both solutions at 12:40 Aliquot 2 (50 uL) extracted from KAB8-7 at 13:20 [data]2653[/data][data]2655[/data] TLCs were eluted with EtOAc/hexane, 4:1, v/v. Stain: KMnO<sub>4</sub> KAB8-8 taken off @ 12:50. KAB8-7 taken off @ 13:25. The reaction mixture was quenched with saturated sodium bicarbonate solution (50 mL) and the organic layer removed. The alkaline aqueous fraction was extracted with EtOAc (3 × 30 mL). The organic layers were combined, dried over magnesium sulfate, filtered, then concentrated under reduced pressure to give the crude products. Crude KAB8-7: 132.7 mg, 175% - yellowish gum + yellow oil. Crude KAB8-8: 89.4 mg, 118% - yellowish solid gum. [b]Recrystallisation[/b] [b]30/01/12.[/b] The crude products of KAB8-7 and KAB8-8 were dissolved in a minimum of hot EtOAc. Hexane was added dropwise until a white precipitate began to form on contact with the hot, yellow EtOAc solution (~1:1, EtOAc/hexane, v/v). The flasks were sealed then placed in the freezer overnight. [b]31/01/12[/b]. Formation of yellow crystals for both KAB8-7 and KAB8-8. Still stored in freezer. [data]2705[/data][data]2707[/data] [b]01/02/12[/b]. The KAB8-8 and KAB8-7 crystals were washed with hexane and filtered to give small orange crystals. KAB8-7 - 102 mg, 83%. KAB8-8 - 69.2 mg, 91%. [data]2733[/data] [b]02/02/12[/b]. <sup>1</sup>H-NMR of the KAB8-8 and KAB8-7 samples confirmed both products as the dimethoxy [i]N[/i]-benzoyl PZQ analogues. TLC of the crystals showed no co-spotting and the spot that was visible under long wave UV (350 nm) was no longer present. TO DO: - TLC crystals against filtrate (see where long wave UV spot ends up). [b][u]Summary and Conclusion[/u][/b] -------------------------------------------------------------- NOTES 30/01/12 - KAB8-8 with the lower catalyst loading probably finished first because of the way I added the acid. The acid solution was added into the MNR10-1/toluene solution with a long needle. The KAB8-7 acid was added to the flask, but not directly into the solution. - The KAB8-8 mixture went to temperature faster; reached temperature in less than 2 min. The KAB8-7 reaction mixture did not reach 90 °C. The reaction was quenched at ~80 °C. NOTES 31/01/12 - KAB8-8 filter paper: 1.0973 g NOTES 01/02/12 - KAB8-7 filter paper 1.1030 g NOTES 02/02/12 - Long wave co-spot was absent. Will TLC filtrate. --------------------------------------------------------------]]></content><html><![CDATA[<i>*PS = Pictet-Spengler</i><br style="clear:left;"/><br style="clear:left;"/><b><u>Background</b></u><br style="clear:left;"/>Repeat of procedure for the preparation of KAB8-5 with reduced catalyst loading.<br style="clear:left;"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/2648/Scheme%20KAB8-7.png" width="550"/><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><br style="clear:left;"/><img src="" width="400"/><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Hazard and Risk Assessment</b></u><br style="clear:left;"/>As for KAB8-5 (<a href="http://www.ourexperiment.org/data/files/2630/HRA%20KAB8-5.pdf" class="ng_url">here</a>)<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/3873/Controls_for_the_AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB85__KAB86.html">Controls for the AgOTf catalysed PS* to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-5 & KAB8-6)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/3660/The_silverI_triflate_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB84.html">The silver(I) triflate catalysed PS to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-4)</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/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><br style="clear:left;"/><br style="clear:left;"/><b><u>Procedure</b></u><br style="clear:left;"/><br style="clear:left;"/><b>Preparation of stock acid</b>: A 0.26 M solution of TfOH in toluene was prepared by mixing TfOH (~195 mg, 1.3 mmol) in toluene (5 mL). It was assumed the TfOH contributed negligible volume.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-7</b>: MNR10-1 (153.9 mg, 0.336 mmol) was dissolved in toluene (32 mL) before the TfOH/toluene mixture (0.39 mL; TfOH = 30 mol%) was added at 12:30 at rt. The mixture was heated to 90 °C.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-8</b>: The procedure was the same as for KAB8-7. MNR10-1 (94.8 mg, 0.207 mmol), toluene (32 mL), TfOH/toluene (0.12 mL; TfOH = 15 mol%). Added at 12:35 at rt, before heated to 90 °C.<br style="clear:left;"/><br style="clear:left;"/>Aliquot 1 (50 uL) extracted from both solutions at 12:40<br style="clear:left;"/>Aliquot 2 (50 uL) extracted from KAB8-7 at 13:20<br style="clear:left;"/><br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2653.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=2653&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of reaction mixtures (1)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2655.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=2655&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-7 reaction mixture (2)</div></div><br style="clear:left;"/>TLCs were eluted with EtOAc/hexane, 4:1, v/v. Stain: KMnO<sub>4</sub><br style="clear:left;"/><br style="clear:left;"/>KAB8-8 taken off @ 12:50.<br style="clear:left;"/>KAB8-7 taken off @ 13:25.<br style="clear:left;"/><br style="clear:left;"/>The reaction mixture was quenched with saturated sodium bicarbonate solution (50 mL) and the organic layer removed. The alkaline aqueous fraction was extracted with EtOAc (3 × 30 mL). The organic layers were combined, dried over magnesium sulfate, filtered, then concentrated under reduced pressure to give the crude products.<br style="clear:left;"/><br style="clear:left;"/>Crude KAB8-7: 132.7 mg, 175% - yellowish gum + yellow oil.<br style="clear:left;"/>Crude KAB8-8: 89.4 mg, 118% - yellowish solid gum.<br style="clear:left;"/><br style="clear:left;"/><b>Recrystallisation</b><br style="clear:left;"/><b>30/01/12.</b> The crude products of KAB8-7 and KAB8-8 were dissolved in a minimum of hot EtOAc. Hexane was added dropwise until a white precipitate began to form on contact with the hot, yellow EtOAc solution (~1:1, EtOAc/hexane, v/v). The flasks were sealed then placed in the freezer overnight.<br style="clear:left;"/><b>31/01/12</b>. Formation of yellow crystals for both KAB8-7 and KAB8-8. Still stored in freezer.<br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2705.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=2705&width=100&height=75&thumb=1); width:100px; height:75px; "></div>KAB8-7 crystals on 31/01/12</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2707.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=2707&width=100&height=75&thumb=1); width:100px; height:75px; "></div>KAB8-8 crystals on 31/01/12</div></div><br style="clear:left;"/><b>01/02/12</b>. The KAB8-8 and KAB8-7 crystals were washed with hexane and filtered to give small orange crystals.<br style="clear:left;"/>KAB8-7 - 102 mg, 83%.<br style="clear:left;"/>KAB8-8 - 69.2 mg, 91%.<br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2733.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=2733&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Left: KAB8-7; Right: KAB8-8</div></div><br style="clear:left;"/><b>02/02/12</b>. <sup>1</sup>H-NMR of the KAB8-8 and KAB8-7 samples confirmed both products as the dimethoxy <i>N</i>-benzoyl PZQ analogues. TLC of the crystals showed no co-spotting and the spot that was visible under long wave UV (350 nm) was no longer present.<br style="clear:left;"/><br style="clear:left;"/>TO DO:<br style="clear:left;"/>- TLC crystals against filtrate (see where long wave UV spot ends up).<br style="clear:left;"/><br style="clear:left;"/><b><u>Summary and Conclusion</u></b><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>--------------------------------------------------------------<br style="clear:left;"/>NOTES 30/01/12<br style="clear:left;"/>- KAB8-8 with the lower catalyst loading probably finished first because of the way I added the acid. The acid solution was added into the MNR10-1/toluene solution with a long needle. The KAB8-7 acid was added to the flask, but not directly into the solution.<br style="clear:left;"/>- The KAB8-8 mixture went to temperature faster; reached temperature in less than 2 min. The KAB8-7 reaction mixture did not reach 90 °C. The reaction was quenched at ~80 °C.<br style="clear:left;"/><br style="clear:left;"/>NOTES 31/01/12<br style="clear:left;"/>- KAB8-8 filter paper: 1.0973 g<br style="clear:left;"/><br style="clear:left;"/>NOTES 01/02/12<br style="clear:left;"/>- KAB8-7 filter paper 1.1030 g<br style="clear:left;"/><br style="clear:left;"/>NOTES 02/02/12<br style="clear:left;"/>- Long wave co-spot was absent. Will TLC filtrate.<br style="clear:left;"/>--------------------------------------------------------------<div class="postTools"><div class="postLinkedBut" onclick="$('#postLinked_3912').fadeIn();">Linked Posts</div></div> <div class="postLinkedItems" id="postLinked_3912"><b>This post is linked by:</b><ul> <li><a href="http://www.ourexperiment.org/racemic_pzq/4087/TfOH_catalysed_PS_reaction_to_give_PZQ_KAB311.html">TfOH catalysed PS* reaction to give PZQ (KAB3-11)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/3873/Controls_for_the_AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB85__KAB86.html">Controls for the AgOTf catalysed PS* to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-5 & KAB8-6)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4080/AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB810.html">AgOTf catalysed PS to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-10)</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/4248/KAB_ExperimentCompound_Index.html">KAB Experiment/Compound Index</a></li></ul></div> ]]></html><datestamp>2012-01-29T23:46:31+00:00</datestamp><timestamp>2012-03-04T08:37:13+00:00</timestamp><blog>6</blog><key>9f2dde9f0f4f1e88273aa60e10f35a0b</key><attached_data><data>https://www.ourexperiment.org/data/2649.xml</data><data>https://www.ourexperiment.org/data/2651.xml</data><data>https://www.ourexperiment.org/data/2653.xml</data><data>https://www.ourexperiment.org/data/2655.xml</data><data>https://www.ourexperiment.org/data/2657.xml</data><data>https://www.ourexperiment.org/data/2705.xml</data><data>https://www.ourexperiment.org/data/2707.xml</data><data>https://www.ourexperiment.org/data/2733.xml</data></attached_data><links><uri>http://www.ourexperiment.org/uri/1d9</uri><permalink>https://www.ourexperiment.org/racemic_pzq/3912/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB87__KAB88.html</permalink></links><formats><format 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current="true">https://www.ourexperiment.org/racemic_pzq/3912/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB87__KAB88.xml?revision=4816</revision><revision>https://www.ourexperiment.org/racemic_pzq/3912/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB87__KAB88.xml?revision=6993</revision></revisions><comments/></post><post><id>3912</id><rid>6993</rid><title/><section>Experiments</section><author><username>plus.google.com-+KatrinaBadiola</username><name>Katrina Badiola</name></author><content><![CDATA[[i]*PS = Pictet-Spengler[/i] [b][u]Background[/b][/u] Repeat of procedure for the preparation of KAB8-5 with reduced catalyst loading. <img src="http://www.ourexperiment.org/data/files/2648/Scheme%20KAB8-7.png" width="550"/>[blog]3936[/blog] <img src="" width="400"/> [b][u]Hazard and Risk Assessment[/b][/u] As for KAB8-5 ([url=http://www.ourexperiment.org/data/files/2630/HRA%20KAB8-5.pdf]here[/url]) [b][u]Previous Related Experiments[/b][/u] [blog]3873[/blog] [blog]3660[/blog] [b][u]Following Experiments[/b][/u] [blog]3936[/blog] [b][u]Procedure[/b][/u] [b]Preparation of stock acid[/b]: A 0.26 M solution of TfOH in toluene was prepared by mixing TfOH (~195 mg, 1.3 mmol) in toluene (5 mL). It was assumed the TfOH contributed negligible volume. [b]KAB8-7[/b]: MNR10-1 (153.9 mg, 0.336 mmol) was dissolved in toluene (32 mL) before the TfOH/toluene mixture (0.39 mL; TfOH = 30 mol%) was added at 12:30 at rt. The mixture was heated to 90 °C. [b]KAB8-8[/b]: The procedure was the same as for KAB8-7. MNR10-1 (94.8 mg, 0.207 mmol), toluene (32 mL), TfOH/toluene (0.12 mL; TfOH = 15 mol%). Added at 12:35 at rt, before heated to 90 °C. Aliquot 1 (50 uL) extracted from both solutions at 12:40 Aliquot 2 (50 uL) extracted from KAB8-7 at 13:20 [data]2653[/data][data]2655[/data] TLCs were eluted with EtOAc/hexane, 4:1, v/v. Stain: KMnO<sub>4</sub> KAB8-8 taken off @ 12:50. KAB8-7 taken off @ 13:25. The reaction mixture was quenched with saturated sodium bicarbonate solution (50 mL) and the organic layer removed. The alkaline aqueous fraction was extracted with EtOAc (3 × 30 mL). The organic layers were combined, dried over magnesium sulfate, filtered, then concentrated under reduced pressure to give the crude products. Crude KAB8-7: 132.7 mg, 175% - yellowish gum + yellow oil. Crude KAB8-8: 89.4 mg, 118% - yellowish solid gum. [b]Recrystallisation[/b] [b]30/01/12.[/b] The crude products of KAB8-7 and KAB8-8 were dissolved in a minimum of hot EtOAc. Hexane was added dropwise until a white precipitate began to form on contact with the hot, yellow EtOAc solution (~1:1, EtOAc/hexane, v/v). The flasks were sealed then placed in the freezer overnight. [b]31/01/12[/b]. Formation of yellow crystals for both KAB8-7 and KAB8-8. Still stored in freezer. [data]2705[/data][data]2707[/data] [b]01/02/12[/b]. The KAB8-8 and KAB8-7 crystals were washed with hexane and filtered to give small orange crystals. KAB8-7 - 102 mg, 83%. KAB8-8 - 69.2 mg, 91%. [data]2733[/data] [b]02/02/12[/b]. <sup>1</sup>H-NMR of the KAB8-8 and KAB8-7 samples confirmed both products as the dimethoxy [i]N[/i]-benzoyl PZQ analogues. TLC of the crystals showed no co-spotting and the spot that was visible under long wave UV (350 nm) was no longer present. TO DO: - TLC crystals against filtrate (see where long wave UV spot ends up). [b][u]Summary and Conclusion[/u][/b] -------------------------------------------------------------- NOTES 30/01/12 - KAB8-8 with the lower catalyst loading probably finished first because of the way I added the acid. The acid solution was added into the MNR10-1/toluene solution with a long needle. The KAB8-7 acid was added to the flask, but not directly into the solution. - The KAB8-8 mixture went to temperature faster; reached temperature in less than 2 min. The KAB8-7 reaction mixture did not reach 90 °C. The reaction was quenched at ~80 °C. NOTES 31/01/12 - KAB8-8 filter paper: 1.0973 g NOTES 01/02/12 - KAB8-7 filter paper 1.1030 g NOTES 02/02/12 - Long wave co-spot was absent. Will TLC filtrate. --------------------------------------------------------------]]></content><html><![CDATA[<i>*PS = Pictet-Spengler</i><br style="clear:left;"/><br style="clear:left;"/><b><u>Background</b></u><br style="clear:left;"/>Repeat of procedure for the preparation of KAB8-5 with reduced catalyst loading.<br style="clear:left;"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/2648/Scheme%20KAB8-7.png" width="550"/><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><br style="clear:left;"/><img src="" width="400"/><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Hazard and Risk Assessment</b></u><br style="clear:left;"/>As for KAB8-5 (<a href="http://www.ourexperiment.org/data/files/2630/HRA%20KAB8-5.pdf" class="ng_url">here</a>)<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/3873/Controls_for_the_AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB85__KAB86.html">Controls for the AgOTf catalysed PS* to give the dimethoxy N-benzoyl PZQ analogue (KAB8-5 & KAB8-6)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/3660/The_silverI_triflate_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB84.html">The silver(I) triflate catalysed PS to give the dimethoxy N-benzoyl PZQ analogue (KAB8-4)</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/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><br style="clear:left;"/><br style="clear:left;"/><b><u>Procedure</b></u><br style="clear:left;"/><br style="clear:left;"/><b>Preparation of stock acid</b>: A 0.26 M solution of TfOH in toluene was prepared by mixing TfOH (~195 mg, 1.3 mmol) in toluene (5 mL). It was assumed the TfOH contributed negligible volume.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-7</b>: MNR10-1 (153.9 mg, 0.336 mmol) was dissolved in toluene (32 mL) before the TfOH/toluene mixture (0.39 mL; TfOH = 30 mol%) was added at 12:30 at rt. The mixture was heated to 90 °C.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-8</b>: The procedure was the same as for KAB8-7. MNR10-1 (94.8 mg, 0.207 mmol), toluene (32 mL), TfOH/toluene (0.12 mL; TfOH = 15 mol%). Added at 12:35 at rt, before heated to 90 °C.<br style="clear:left;"/><br style="clear:left;"/>Aliquot 1 (50 uL) extracted from both solutions at 12:40<br style="clear:left;"/>Aliquot 2 (50 uL) extracted from KAB8-7 at 13:20<br style="clear:left;"/><br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2653.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=2653&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of reaction mixtures (1)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2655.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=2655&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-7 reaction mixture (2)</div><br style="clear:left;"/>TLCs were eluted with EtOAc/hexane, 4:1, v/v. Stain: KMnO<sub>4</sub><br style="clear:left;"/><br style="clear:left;"/>KAB8-8 taken off @ 12:50.<br style="clear:left;"/>KAB8-7 taken off @ 13:25.<br style="clear:left;"/><br style="clear:left;"/>The reaction mixture was quenched with saturated sodium bicarbonate solution (50 mL) and the organic layer removed. The alkaline aqueous fraction was extracted with EtOAc (3 × 30 mL). The organic layers were combined, dried over magnesium sulfate, filtered, then concentrated under reduced pressure to give the crude products.<br style="clear:left;"/><br style="clear:left;"/>Crude KAB8-7: 132.7 mg, 175% - yellowish gum + yellow oil.<br style="clear:left;"/>Crude KAB8-8: 89.4 mg, 118% - yellowish solid gum.<br style="clear:left;"/><br style="clear:left;"/><b>Recrystallisation</b><br style="clear:left;"/><b>30/01/12.</b> The crude products of KAB8-7 and KAB8-8 were dissolved in a minimum of hot EtOAc. Hexane was added dropwise until a white precipitate began to form on contact with the hot, yellow EtOAc solution (~1:1, EtOAc/hexane, v/v). The flasks were sealed then placed in the freezer overnight.<br style="clear:left;"/><b>31/01/12</b>. Formation of yellow crystals for both KAB8-7 and KAB8-8. Still stored in freezer.<br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2705.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=2705&width=100&height=75&thumb=1); width:100px; height:75px; "></div>KAB8-7 crystals on 31/01/12</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2707.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=2707&width=100&height=75&thumb=1); width:100px; height:75px; "></div>KAB8-8 crystals on 31/01/12</div><br style="clear:left;"/><b>01/02/12</b>. The KAB8-8 and KAB8-7 crystals were washed with hexane and filtered to give small orange crystals.<br style="clear:left;"/>KAB8-7 - 102 mg, 83%.<br style="clear:left;"/>KAB8-8 - 69.2 mg, 91%.<br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2733.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=2733&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Left: KAB8-7; Right: KAB8-8</div><br style="clear:left;"/><b>02/02/12</b>. <sup>1</sup>H-NMR of the KAB8-8 and KAB8-7 samples confirmed both products as the dimethoxy <i>N</i>-benzoyl PZQ analogues. TLC of the crystals showed no co-spotting and the spot that was visible under long wave UV (350 nm) was no longer present.<br style="clear:left;"/><br style="clear:left;"/>TO DO:<br style="clear:left;"/>- TLC crystals against filtrate (see where long wave UV spot ends up).<br style="clear:left;"/><br style="clear:left;"/><b><u>Summary and Conclusion</u></b><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>--------------------------------------------------------------<br style="clear:left;"/>NOTES 30/01/12<br style="clear:left;"/>- KAB8-8 with the lower catalyst loading probably finished first because of the way I added the acid. The acid solution was added into the MNR10-1/toluene solution with a long needle. The KAB8-7 acid was added to the flask, but not directly into the solution.<br style="clear:left;"/>- The KAB8-8 mixture went to temperature faster; reached temperature in less than 2 min. The KAB8-7 reaction mixture did not reach 90 °C. The reaction was quenched at ~80 °C.<br style="clear:left;"/><br style="clear:left;"/>NOTES 31/01/12<br style="clear:left;"/>- KAB8-8 filter paper: 1.0973 g<br style="clear:left;"/><br style="clear:left;"/>NOTES 01/02/12<br style="clear:left;"/>- KAB8-7 filter paper 1.1030 g<br style="clear:left;"/><br style="clear:left;"/>NOTES 02/02/12<br style="clear:left;"/>- Long wave co-spot was absent. Will TLC filtrate.<br style="clear:left;"/>--------------------------------------------------------------<div class="postTools"><div class="postLinkedBut" onclick="$('#postLinked_3912').fadeIn();">Linked Entries</div></div> <div class="postLinkedItems" id="postLinked_3912"><b>This entry is linked by:</b><ul> <li><a href="http://www.ourexperiment.org/racemic_pzq/4087/TfOH_catalysed_PS_reaction_to_give_PZQ_KAB311.html">TfOH catalysed PS* reaction to give PZQ (KAB3-11)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/3873/Controls_for_the_AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB85__KAB86.html">Controls for the AgOTf catalysed PS* to give the dimethoxy N-benzoyl PZQ analogue (KAB8-5 & KAB8-6)</a></li><li><a href="http://www.ourexperiment.org/racemic_pzq/4080/AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB810.html">AgOTf catalysed PS to give the dimethoxy N-benzoyl PZQ analogue (KAB8-10)</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/4248/KAB_ExperimentCompound_Index.html">KAB Experiment/Compound Index</a></li></ul></div> 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