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38734639<section>Experiments</section><author><username>plus.google.com-+KatrinaBadiola</username><name>Katrina Badiola</name></author><content><![CDATA[[i]*PS = Pictet-Spengler[/i] *****Experiment concluded on 30/01/12. [b][u]Background[/b][/u] <img src="http://www.ourexperiment.org/data/files/2628/Scheme%20KAB8-5.png" width="550"/> <img src="http://www.ourexperiment.org/data/files/2632/Table%20KAB8-5.jpg" width="400"/> <img src="http://www.ourexperiment.org/data/files/2634/Table%20KAB8-6.jpg" width="400"/> [b][u]Hazard and Risk Assessment[/b][/u] [data]2631[/data] [b][u]Previous Related Experiments[/b][/u] [blog]3660[/blog] [blog]3598[/blog] [blog]3566[/blog] [b][u]Following Experiments[/b][/u] [blog]3912[/blog] [b][u]Procedure[/b][/u] Start: 27/01/12 Finish: 30/01/12 The MNR10-1 starting material was dissolved in toluene before the addition of either triflic acid (TfOH) or silver trifluoroacetate. [b]KAB8-5.[/b] MNR10-1 - 0.1018 g, 0.222 mmol Toluene - 34 mL TfOH - 2 drops, ~20 mg, 60 mol% [b]KAB8-6.[/b] MNR10 - 97.8 mg Toluene - 34 mL AgCO<sub>2</sub>CF<sub>3</sub> - 28.1 mg, 60 mol% Both mixtures were heated to 90 °C from 10:10. The reaction progress was monitored by TLC. Aliquots (0.1 mL) were extracted and run against the MNR10-1 starting material and the expected product (identical to KAB8-1). [b]27/01/12[/b] 10:40 - Aliquot 1 12:20 - Aliquot 2 15:05 - Aliquot 3 17:20 - Aliquot 4 [b]30/01/12[/b] 08:45 - Aliquot 5 [b]Monitoring the Reaction Progress by TLC[/b] All TLCs were eluted with EtOAc/hexane, 4:1, v/v, with a KMnO<sub>4</sub> stain. [data]2637[/data][data]2643[/data][data]2645[/data][data]2647[/data] [i]TLC Legend (Aliquot numbers indicated by the circled number at the bottom of the plate; from L to R): [b]8-5[/b] - Aliquot of the KAB8-5 reaction mixture; [b]Co[/b] - Co-spot of the extracted KAB8-5 aliquot, the MNR10-1 starting material and the expected product; [b]SM[/b] - The MNR10-1 starting material; [b]8-1[/b] - The expected product, identical to KAB8-1; [b]Co[/b] - Co-spot of the extracted KAB8-6 aliquot, the starting material and the expected product; [b]8-6[/b] - The extracted KAB8-6 aliquot.[/i] [b]Work-Up - KAB8-5[/b] [b]27/01/12[/b]. The reaction mixture was taken off heat and allowed to cool at 11:00. The pH of the reaction mixture was 5 before it was quenched with saturated sodium bicarbonate solution (50 mL). The organic fraction was set aside and the aqueous layer was extracted withe EtOAc (4 × 30 mL). The organic layers were combined (cloudy, off-white solution) then dried over magnesium sulfate, after which the solution turned clear and colourless. The combined organic layers were then concentrated under reduced pressure to give an off-white/yellowish residue, which was dissolved in EtOAc. The pale yellow solution was passed through a silica pad. The filtrate was collected and concentrated [i]in vacuo[/i] to give crude KAB8-5 as an off-white, gummy solid (49 mg, 60 %). The solid was re-crystallised from EtOAc/hexane and stored in the freezer over the weekend. [b]02/01/12[/b]. The white crystals were filtered and washed with hexane to give KAB8-5, the dimethoxy [i]N[/i]-benzoyl PZQ analogue as off white crystals (91.3 mg, 112%). The NMR showed some solvent contamination (hexane and EtOAc). [b]Work-Up - KAB8-6 - 30/01/12[/b] Final TLC (5) of the reaction mixture, taken 70 hours after heating, suggested the major component was the MNR10-1 starting material. However, there were some unknown spots with R<sub>f</sub> unlike the expected product, the enediamide intermediate or the starting material. No workup was performed and product was taken no further. [b][u]Conclusion[/u][/b] TO DO: - Dry crystals under high vacuum and re-calculate yield. - Upload NMR - Write conclusion. [b][u]References[/u][/b] Todd, M. H., Ndubaku, C. & Bartlett, P. A., [i]J. Org. Chem.[/i] [b]2002[/b], [i]67[/i], 3985-3988 - DOI: 10.1021/jo010990m ([url=http://dx.doi.org/10.1021/jo010990m]Paper[/url]) -------------------------------------------------------------- NOTES 27/01/12 - Estimated TfOH mass by weighing 10 drops then 5 drops: 10 drops = 0.1029 g (10.3 mg/drop); 5 drops = 48.3 mg (9.66 mg/drop). - A white solid precipitated out, before quickly dissolving, immediately after the addition of TfOH to the MNR10-1/toluene mixture. - The crude KAB8-5 appeared solid-ish. Attempt to recrystallise from EtOAc/hexane did not work. TLC of the crude product showed impurities, so the product was filtered through a silica pad. NOTES 28/01/12 - Check reactivity of reaction components. --------------------------------------------------------------]]></content><html><![CDATA[<i>*PS = Pictet-Spengler</i><br style="clear:left;"/><br style="clear:left;"/>*****Experiment concluded on 30/01/12.<br style="clear:left;"/><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/2628/Scheme%20KAB8-5.png" width="550"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/2632/Table%20KAB8-5.jpg" width="400"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/2634/Table%20KAB8-6.jpg" width="400"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Hazard and Risk Assessment</b></u><br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2631.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=2631&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Hazard and Risk Assessment</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/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;"/><a href="http://www.ourexperiment.org/racemic_pzq/3598/SilverI_triflate_catalysed_preparation_of_the_dimethoxy_Nbenzoyl_PZQ_enediamide_KAB112.html">Silver(I) triflate catalysed preparation of the dimethoxy <i>N</i>-benzoyl PZQ enediamide (KAB11-2)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/3566/Lewis_acid_catalysed_preparation_of_the_dimethoxy_Nbenzoyl_PZQ_enediamide_KAB111.html">Lewis acid catalysed preparation of the dimethoxy <i>N</i>-benzoyl PZQ enediamide (KAB11-1)</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/3912/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB87__KAB88.html">TfOH catalysed PS* reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-7 & KAB8-8)</a><br style="clear:left;"/><br style="clear:left;"/><b><u>Procedure</b></u><br style="clear:left;"/><br style="clear:left;"/>Start: 27/01/12<br style="clear:left;"/>Finish: 30/01/12<br style="clear:left;"/><br style="clear:left;"/>The MNR10-1 starting material was dissolved in toluene before the addition of either triflic acid (TfOH) or silver trifluoroacetate.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-5.</b> <br style="clear:left;"/>MNR10-1 - 0.1018 g, 0.222 mmol<br style="clear:left;"/>Toluene - 34 mL<br style="clear:left;"/>TfOH - 2 drops, ~20 mg, 60 mol%<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-6.</b><br style="clear:left;"/>MNR10 - 97.8 mg<br style="clear:left;"/>Toluene - 34 mL<br style="clear:left;"/>AgCO<sub>2</sub>CF<sub>3</sub> - 28.1 mg, 60 mol%<br style="clear:left;"/><br style="clear:left;"/>Both mixtures were heated to 90 °C from 10:10. The reaction progress was monitored by TLC. Aliquots (0.1 mL) were extracted and run against the MNR10-1 starting material and the expected product (identical to KAB8-1).<br style="clear:left;"/><br style="clear:left;"/><b>27/01/12</b><br style="clear:left;"/>10:40 - Aliquot 1<br style="clear:left;"/>12:20 - Aliquot 2<br style="clear:left;"/>15:05 - Aliquot 3<br style="clear:left;"/>17:20 - Aliquot 4<br style="clear:left;"/><br style="clear:left;"/><b>30/01/12</b><br style="clear:left;"/>08:45 - Aliquot 5<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, 4:1, v/v, with a KMnO<sub>4</sub> stain.<br style="clear:left;"/><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2637.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=2637&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/2643.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=2643&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-6 reaction mixture (2)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2645.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=2645&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of reaction mixtures (3)</div></div><div style="float:left;"><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2647.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=2647&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of reaction mixtures (4)</div></div><br style="clear:left;"/><i>TLC Legend (Aliquot numbers indicated by the circled number at the bottom of the plate; from L to R): <b>8-5</b> - Aliquot of the KAB8-5 reaction mixture; <b>Co</b> - Co-spot of the extracted KAB8-5 aliquot, the MNR10-1 starting material and the expected product; <b>SM</b> - The MNR10-1 starting material; <b>8-1</b> - The expected product, identical to KAB8-1; <b>Co</b> - Co-spot of the extracted KAB8-6 aliquot, the starting material and the expected product; <b>8-6</b> - The extracted KAB8-6 aliquot.</i><br style="clear:left;"/><br style="clear:left;"/><b>Work-Up - KAB8-5</b><br style="clear:left;"/><b>27/01/12</b>. The reaction mixture was taken off heat and allowed to cool at 11:00. The pH of the reaction mixture was 5 before it was quenched with saturated sodium bicarbonate solution (50 mL). The organic fraction was set aside and the aqueous layer was extracted withe EtOAc (4 × 30 mL). The organic layers were combined (cloudy, off-white solution) then dried over magnesium sulfate, after which the solution turned clear and colourless. The combined organic layers were then concentrated under reduced pressure to give an off-white/yellowish residue, which was dissolved in EtOAc. The pale yellow solution was passed through a silica pad. The filtrate was collected and concentrated <i>in vacuo</i> to give crude KAB8-5 as an off-white, gummy solid (49 mg, 60 %). The solid was re-crystallised from EtOAc/hexane and stored in the freezer over the weekend.<br style="clear:left;"/><b>02/01/12</b>. The white crystals were filtered and washed with hexane to give KAB8-5, the dimethoxy <i>N</i>-benzoyl PZQ analogue as off white crystals (91.3 mg, 112%).<br style="clear:left;"/>The NMR showed some solvent contamination (hexane and EtOAc).<br style="clear:left;"/><br style="clear:left;"/><b>Work-Up - KAB8-6 - 30/01/12</b><br style="clear:left;"/>Final TLC (5) of the reaction mixture, taken 70 hours after heating, suggested the major component was the MNR10-1 starting material. However, there were some unknown spots with R<sub>f</sub> unlike the expected product, the enediamide intermediate or the starting material.<br style="clear:left;"/>No workup was performed and product was taken no further.<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Conclusion</u></b><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>TO DO:<br style="clear:left;"/>- Dry crystals under high vacuum and re-calculate yield.<br style="clear:left;"/>- Upload NMR<br style="clear:left;"/>- Write conclusion.<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><b><u>References</u></b><br style="clear:left;"/>Todd, M. H., Ndubaku, C. & Bartlett, P. A., <i>J. Org. Chem.</i> <b>2002</b>, <i>67</i>, 3985-3988 - DOI: 10.1021/jo010990m (<a href="http://dx.doi.org/10.1021/jo010990m" class="ng_url">Paper</a>)<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>--------------------------------------------------------------<br style="clear:left;"/>NOTES 27/01/12<br style="clear:left;"/>- Estimated TfOH mass by weighing 10 drops then 5 drops: 10 drops = 0.1029 g (10.3 mg/drop); 5 drops = 48.3 mg (9.66 mg/drop).<br style="clear:left;"/>- A white solid precipitated out, before quickly dissolving, immediately after the addition of TfOH to the MNR10-1/toluene mixture.<br style="clear:left;"/>- The crude KAB8-5 appeared solid-ish. Attempt to recrystallise from EtOAc/hexane did not work. TLC of the crude product showed impurities, so the product was filtered through a silica pad.<br style="clear:left;"/><br style="clear:left;"/>NOTES 28/01/12<br style="clear:left;"/>- Check reactivity of reaction components.<br style="clear:left;"/>--------------------------------------------------------------<div class="postTools"><div class="postLinkedBut" onclick="$('#postLinked_3873').fadeIn();">Linked Posts</div></div> <div class="postLinkedItems" id="postLinked_3873"><b>This post is linked by:</b><ul> <li><a href="http://www.ourexperiment.org/racemic_pzq/3912/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB87__KAB88.html">TfOH catalysed PS* reaction to give the dimethoxy <i>N</i>-benzoyl PZQ analogue (KAB8-7 & KAB8-8)</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> 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current="true">https://www.ourexperiment.org/racemic_pzq/3873/Controls_for_the_AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB85__KAB86.xml?revision=4639</revision><revision>https://www.ourexperiment.org/racemic_pzq/3873/Controls_for_the_AgOTf_catalysed_PS_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB85__KAB86.xml?revision=6992</revision></revisions><comments/></post><post><id>3873</id><rid>6992</rid><title/><section>Experiments</section><author><username>plus.google.com-+KatrinaBadiola</username><name>Katrina Badiola</name></author><content><![CDATA[[i]*PS = Pictet-Spengler[/i] *****Experiment concluded on 30/01/12. [b][u]Background[/b][/u] <img src="http://www.ourexperiment.org/data/files/2628/Scheme%20KAB8-5.png" width="550"/> <img src="http://www.ourexperiment.org/data/files/2632/Table%20KAB8-5.jpg" width="400"/> <img src="http://www.ourexperiment.org/data/files/2634/Table%20KAB8-6.jpg" width="400"/> [b][u]Hazard and Risk Assessment[/b][/u] [data]2631[/data] [b][u]Previous Related Experiments[/b][/u] [blog]3660[/blog] [blog]3598[/blog] [blog]3566[/blog] [b][u]Following Experiments[/b][/u] [blog]3912[/blog] [b][u]Procedure[/b][/u] Start: 27/01/12 Finish: 30/01/12 The MNR10-1 starting material was dissolved in toluene before the addition of either triflic acid (TfOH) or silver trifluoroacetate. [b]KAB8-5.[/b] MNR10-1 - 0.1018 g, 0.222 mmol Toluene - 34 mL TfOH - 2 drops, ~20 mg, 60 mol% [b]KAB8-6.[/b] MNR10 - 97.8 mg Toluene - 34 mL AgCO<sub>2</sub>CF<sub>3</sub> - 28.1 mg, 60 mol% Both mixtures were heated to 90 °C from 10:10. The reaction progress was monitored by TLC. Aliquots (0.1 mL) were extracted and run against the MNR10-1 starting material and the expected product (identical to KAB8-1). [b]27/01/12[/b] 10:40 - Aliquot 1 12:20 - Aliquot 2 15:05 - Aliquot 3 17:20 - Aliquot 4 [b]30/01/12[/b] 08:45 - Aliquot 5 [b]Monitoring the Reaction Progress by TLC[/b] All TLCs were eluted with EtOAc/hexane, 4:1, v/v, with a KMnO<sub>4</sub> stain. [data]2637[/data][data]2643[/data][data]2645[/data][data]2647[/data] [i]TLC Legend (Aliquot numbers indicated by the circled number at the bottom of the plate; from L to R): [b]8-5[/b] - Aliquot of the KAB8-5 reaction mixture; [b]Co[/b] - Co-spot of the extracted KAB8-5 aliquot, the MNR10-1 starting material and the expected product; [b]SM[/b] - The MNR10-1 starting material; [b]8-1[/b] - The expected product, identical to KAB8-1; [b]Co[/b] - Co-spot of the extracted KAB8-6 aliquot, the starting material and the expected product; [b]8-6[/b] - The extracted KAB8-6 aliquot.[/i] [b]Work-Up - KAB8-5[/b] [b]27/01/12[/b]. The reaction mixture was taken off heat and allowed to cool at 11:00. The pH of the reaction mixture was 5 before it was quenched with saturated sodium bicarbonate solution (50 mL). The organic fraction was set aside and the aqueous layer was extracted withe EtOAc (4 × 30 mL). The organic layers were combined (cloudy, off-white solution) then dried over magnesium sulfate, after which the solution turned clear and colourless. The combined organic layers were then concentrated under reduced pressure to give an off-white/yellowish residue, which was dissolved in EtOAc. The pale yellow solution was passed through a silica pad. The filtrate was collected and concentrated [i]in vacuo[/i] to give crude KAB8-5 as an off-white, gummy solid (49 mg, 60 %). The solid was re-crystallised from EtOAc/hexane and stored in the freezer over the weekend. [b]02/01/12[/b]. The white crystals were filtered and washed with hexane to give KAB8-5, the dimethoxy [i]N[/i]-benzoyl PZQ analogue as off white crystals (91.3 mg, 112%). The NMR showed some solvent contamination (hexane and EtOAc). [b]Work-Up - KAB8-6 - 30/01/12[/b] Final TLC (5) of the reaction mixture, taken 70 hours after heating, suggested the major component was the MNR10-1 starting material. However, there were some unknown spots with R<sub>f</sub> unlike the expected product, the enediamide intermediate or the starting material. No workup was performed and product was taken no further. [b][u]Conclusion[/u][/b] TO DO: - Dry crystals under high vacuum and re-calculate yield. - Upload NMR - Write conclusion. [b][u]References[/u][/b] Todd, M. H., Ndubaku, C. & Bartlett, P. A., [i]J. Org. Chem.[/i] [b]2002[/b], [i]67[/i], 3985-3988 - DOI: 10.1021/jo010990m ([url=http://dx.doi.org/10.1021/jo010990m]Paper[/url]) -------------------------------------------------------------- NOTES 27/01/12 - Estimated TfOH mass by weighing 10 drops then 5 drops: 10 drops = 0.1029 g (10.3 mg/drop); 5 drops = 48.3 mg (9.66 mg/drop). - A white solid precipitated out, before quickly dissolving, immediately after the addition of TfOH to the MNR10-1/toluene mixture. - The crude KAB8-5 appeared solid-ish. Attempt to recrystallise from EtOAc/hexane did not work. TLC of the crude product showed impurities, so the product was filtered through a silica pad. NOTES 28/01/12 - Check reactivity of reaction components. --------------------------------------------------------------]]></content><html><![CDATA[<i>*PS = Pictet-Spengler</i><br style="clear:left;"/><br style="clear:left;"/>*****Experiment concluded on 30/01/12.<br style="clear:left;"/><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/2628/Scheme%20KAB8-5.png" width="550"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/2632/Table%20KAB8-5.jpg" width="400"/><br style="clear:left;"/><img src="http://www.ourexperiment.org/data/files/2634/Table%20KAB8-6.jpg" width="400"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Hazard and Risk Assessment</b></u><br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2631.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=2631&width=100&height=75&thumb=1); width:100px; height:75px; "></div>Hazard and Risk Assessment</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/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;"/><a href="http://www.ourexperiment.org/racemic_pzq/3598/SilverI_triflate_catalysed_preparation_of_the_dimethoxy_Nbenzoyl_PZQ_enediamide_KAB112.html">Silver(I) triflate catalysed preparation of the dimethoxy N-benzoyl PZQ enediamide (KAB11-2)</a><br style="clear:left;"/><a href="http://www.ourexperiment.org/racemic_pzq/3566/Lewis_acid_catalysed_preparation_of_the_dimethoxy_Nbenzoyl_PZQ_enediamide_KAB111.html">Lewis acid catalysed preparation of the dimethoxy N-benzoyl PZQ enediamide (KAB11-1)</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/3912/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB87__KAB88.html">TfOH catalysed PS* reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-7 & KAB8-8)</a><br style="clear:left;"/><br style="clear:left;"/><b><u>Procedure</b></u><br style="clear:left;"/><br style="clear:left;"/>Start: 27/01/12<br style="clear:left;"/>Finish: 30/01/12<br style="clear:left;"/><br style="clear:left;"/>The MNR10-1 starting material was dissolved in toluene before the addition of either triflic acid (TfOH) or silver trifluoroacetate.<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-5.</b> <br style="clear:left;"/>MNR10-1 - 0.1018 g, 0.222 mmol<br style="clear:left;"/>Toluene - 34 mL<br style="clear:left;"/>TfOH - 2 drops, ~20 mg, 60 mol%<br style="clear:left;"/><br style="clear:left;"/><b>KAB8-6.</b><br style="clear:left;"/>MNR10 - 97.8 mg<br style="clear:left;"/>Toluene - 34 mL<br style="clear:left;"/>AgCO<sub>2</sub>CF<sub>3</sub> - 28.1 mg, 60 mol%<br style="clear:left;"/><br style="clear:left;"/>Both mixtures were heated to 90 °C from 10:10. The reaction progress was monitored by TLC. Aliquots (0.1 mL) were extracted and run against the MNR10-1 starting material and the expected product (identical to KAB8-1).<br style="clear:left;"/><br style="clear:left;"/><b>27/01/12</b><br style="clear:left;"/>10:40 - Aliquot 1<br style="clear:left;"/>12:20 - Aliquot 2<br style="clear:left;"/>15:05 - Aliquot 3<br style="clear:left;"/>17:20 - Aliquot 4<br style="clear:left;"/><br style="clear:left;"/><b>30/01/12</b><br style="clear:left;"/>08:45 - Aliquot 5<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, 4:1, v/v, with a KMnO<sub>4</sub> stain.<br style="clear:left;"/><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2637.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=2637&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/2643.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=2643&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of KAB8-6 reaction mixture (2)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2645.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=2645&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of reaction mixtures (3)</div><div class="dataPic datathumb" onclick="javascript:var blob = window.open('/data/2647.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=2647&width=100&height=75&thumb=1); width:100px; height:75px; "></div>TLC of reaction mixtures (4)</div><br style="clear:left;"/><i>TLC Legend (Aliquot numbers indicated by the circled number at the bottom of the plate; from L to R): <b>8-5</b> - Aliquot of the KAB8-5 reaction mixture; <b>Co</b> - Co-spot of the extracted KAB8-5 aliquot, the MNR10-1 starting material and the expected product; <b>SM</b> - The MNR10-1 starting material; <b>8-1</b> - The expected product, identical to KAB8-1; <b>Co</b> - Co-spot of the extracted KAB8-6 aliquot, the starting material and the expected product; <b>8-6</b> - The extracted KAB8-6 aliquot.</i><br style="clear:left;"/><br style="clear:left;"/><b>Work-Up - KAB8-5</b><br style="clear:left;"/><b>27/01/12</b>. The reaction mixture was taken off heat and allowed to cool at 11:00. The pH of the reaction mixture was 5 before it was quenched with saturated sodium bicarbonate solution (50 mL). The organic fraction was set aside and the aqueous layer was extracted withe EtOAc (4 × 30 mL). The organic layers were combined (cloudy, off-white solution) then dried over magnesium sulfate, after which the solution turned clear and colourless. The combined organic layers were then concentrated under reduced pressure to give an off-white/yellowish residue, which was dissolved in EtOAc. The pale yellow solution was passed through a silica pad. The filtrate was collected and concentrated <i>in vacuo</i> to give crude KAB8-5 as an off-white, gummy solid (49 mg, 60 %). The solid was re-crystallised from EtOAc/hexane and stored in the freezer over the weekend.<br style="clear:left;"/><b>02/01/12</b>. The white crystals were filtered and washed with hexane to give KAB8-5, the dimethoxy <i>N</i>-benzoyl PZQ analogue as off white crystals (91.3 mg, 112%).<br style="clear:left;"/>The NMR showed some solvent contamination (hexane and EtOAc).<br style="clear:left;"/><br style="clear:left;"/><b>Work-Up - KAB8-6 - 30/01/12</b><br style="clear:left;"/>Final TLC (5) of the reaction mixture, taken 70 hours after heating, suggested the major component was the MNR10-1 starting material. However, there were some unknown spots with R<sub>f</sub> unlike the expected product, the enediamide intermediate or the starting material.<br style="clear:left;"/>No workup was performed and product was taken no further.<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><b><u>Conclusion</u></b><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>TO DO:<br style="clear:left;"/>- Dry crystals under high vacuum and re-calculate yield.<br style="clear:left;"/>- Upload NMR<br style="clear:left;"/>- Write conclusion.<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/><b><u>References</u></b><br style="clear:left;"/>Todd, M. H., Ndubaku, C. & Bartlett, P. A., <i>J. Org. Chem.</i> <b>2002</b>, <i>67</i>, 3985-3988 - DOI: 10.1021/jo010990m (<a href="http://dx.doi.org/10.1021/jo010990m" class="ng_url">Paper</a>)<br style="clear:left;"/><br style="clear:left;"/><br style="clear:left;"/>--------------------------------------------------------------<br style="clear:left;"/>NOTES 27/01/12<br style="clear:left;"/>- Estimated TfOH mass by weighing 10 drops then 5 drops: 10 drops = 0.1029 g (10.3 mg/drop); 5 drops = 48.3 mg (9.66 mg/drop).<br style="clear:left;"/>- A white solid precipitated out, before quickly dissolving, immediately after the addition of TfOH to the MNR10-1/toluene mixture.<br style="clear:left;"/>- The crude KAB8-5 appeared solid-ish. Attempt to recrystallise from EtOAc/hexane did not work. TLC of the crude product showed impurities, so the product was filtered through a silica pad.<br style="clear:left;"/><br style="clear:left;"/>NOTES 28/01/12<br style="clear:left;"/>- Check reactivity of reaction components.<br style="clear:left;"/>--------------------------------------------------------------<div class="postTools"><div class="postLinkedBut" onclick="$('#postLinked_3873').fadeIn();">Linked Entries</div></div> <div class="postLinkedItems" id="postLinked_3873"><b>This entry is linked by:</b><ul> <li><a href="http://www.ourexperiment.org/racemic_pzq/3912/TfOH_catalysed_PS_reaction_to_give_the_dimethoxy_Nbenzoyl_PZQ_analogue_KAB87__KAB88.html">TfOH catalysed PS* reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-7 & KAB8-8)</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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