Triethylamine → N-(3-phenoxy)propionyl-proline methyl ester

Participants

Reaction Steps

Proline methyl ester hydrochloride (3.4 g), 3-phenoxypropionic acid (3.4 g) and triethylamine (2.8 ml) were suspended in dry methylene chloride (30 ml). To the cooled suspension, WSCD HCl (N-ethyl-N',N'-dimethylaminopropyl-carbodiimide hydrochloride) (3.9 g) was added. Under cooling, the mixture was stirred for 1 hour, and after allowing the mixture to warm to room temperature, it was again stirred for 18 horus. The stirred mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under vacuum. The resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: chloroform) to obtain the end compound as an oil (3.7 g).

Provenance & Evidence