Triethylamine → benzyl 2(S)-[N-(2-morpholinocarbonylethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 2(S)-hydroxy-3-phenylpropionate (513 mg) in dry tetrahydrofuran (10 ml) was added trichloromethyl chloroformate (0.244 ml). The mixture was refluxed for 18 hours. The mixture was cooled to 0° C., and a solution of 4-(N-methyl-β-alanyl)morpholine trifluoroacetic acid salt (1.44 g) and triethylamine (701 mg) in dry tetrahydrofuran (10 ml) was added thereto. The mixture was stirred at ambient temperature for 2 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (50 ml). The solution was washed with 50% hydrochloric acid, 1M sodium bicarbonate solution and water successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica-gel column chromatography (50% ethyl acetate in n-hexane as eluent) to give benzyl 2(S)-[N-(2-morpholinocarbonylethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate (726 mg) as an oil.

Provenance & Evidence