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17th January 2012 @ 04:10
Experiment concluded on 18/01/12

Test reaction for the attempted isolation of the enediamide intermediate in the Pictet-Spengler reaction to give the dimethoxy PZQ analogues. Monitoring by TLC.


Hazard and Risk Assessment
Hazard and Risk Assessment KAB11-1

Following Experiments
Silver(I) triflate catalysed preparation of the dimethoxy N-benzoyl PZQ enediamide (KAB11-2)


A mixture of MNR10-1 (12 mg, 26 umol) and silver trifluoromethanesulfonate (3.9 mg, 58 mol%) in toluene (120 uL) was stirred at room temperature from 16:15.
Initial TLC suggested a mixture of the expected enediamide, KAB11-1, and the starting material, MNR10-1. Four TLCs of the reaction mixture were run in an attempt to confirm formation of the enediamide, however the TLCs showed varying Rf values, some corresponding to the starting material, and others slightly higher or lower. The reaction mixture was left to stir overnight at rt.

A TLC was run of the reaction mixture. The result was similar to the inconclusive TLCs run last night. It is possible that the extraction of the sample for TLC significantly altered the composition of the reaction due to its low volume.
The result was inconclusive and the reaction was terminated. See follow up experiment (KAB11-2).
Linked Posts
Attached Files
Scheme KAB11-1
Hazard and Risk Assessment KAB11-1
Table KAB11-1
Table KAB11-1 (fixed)