Triethylamine → (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl) phenyl)-3-phenylpropanamide

Participants

Reaction Steps

Triethylamine (480 μl) and pivaloyl chloride (175 μl) were added to a solution of (RS)-2-(4-chlorobenzenesulfonylamino)-3-phenylpropanoic acid (301.7 mg) in THF (5 ml), and the whole was stirred for 2 hours. After methyl 4-aminophenylpropionate hydrochloride (229.8 mg) was added, the whole was stirred at room temperature overnight. The reaction mixture was poured into a saturated saline solution and extracted with ethyl acetate. The combined ethyl acetate layers were washed with a saturated saline solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure to obtain a yellow oil. The product was purified by column chromatography (silica gel 50 g, hexane/ethyl acetate=3/1) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(2-methoxycarbonylethyl) phenyl)-3-phenylpropanamide (40.4 mg).

Provenance & Evidence