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30th May 2013 @ 00:46

Repeated to collect data for paper - see original experiment Coupling of pyrrole acid chloride PMY 32-2 and glycinamide (PMY 31-5) but attempted with EDCI and HOBt for convenience.

Procedure:

AEW 10-1 (51 mg, 0.22 mmol, 1 equiv.) was dissolved in CH2Cl2 (2.2 mL) under Argon. EDC (51 mg, 0.26 mmol, 1.2 equiv.) and HOBt (3 mg, 0.02 mmol. 0.1 equiv.) were added and the yellow solution stirred at room temperature for 15 minutes under Argon. Glycinamide hydrochloride (24 mg, 0.22 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature . No product observed after 1 h or 20 h. DIPEA (0.09 mL, 0.15 mmol, 2.3 equiv.) was added and the white globules in the orange solution dispersed and a white solid crashed out of the mixture. Reaction mixture left to stir at room temperature o/n. Possible roduct observed by TLC. Work up CH2Cl2 and a saturated aqueous solution of NaHCO3, brine, MgSO4, filtered and evaporated.

CH2Clbottle did not contain CH2Cl2!! but seemingly strong acid! 1H NMR consequently shows some decomposition: reaction thrown in waste.

Data:

 

Hazard and Risk Assessment:

See: Amidation of pyrrole acid with dimethylamine (AEW 16-1) and Coupling of pyrrole acid chloride PMY 32-2 and glycinamide (PMY 31-5)

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AEW 59-1.png