Diethyl Pyrocarbonate → N-(3-hydroxy-4-methoxycarbonylbenzyl)-3-(3-indolyl)propanamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-indolyl)propanoic acid [II: R1 =R3 =H, R2 =(CH2)2COOH] (1.50 g), triethylamine (10 mL) and crude methyl 4-(aminomethyl)-2-hydroxybenzoate hydrochloride (3.46 g) in DMF (20 mL) was stirred at 20° C. for 10 minutes, then cooled to 0° C. DEPC (98%, 1.47 mL) was added, then the mixture was stirred at 20° C. for 17 hours. Workup and chromatography on silica gel, eluting with EtOAc:light petroleum (1:1) gave N-(3-hydroxy-4-methoxycarbonylbenzyl)-3-(3-indolyl)propanamide [II: R1 =R3 =H, R2 =(CH2)2CONHCH2Ph{3-OH, 4-COOMe}] (1.40 g, 50%); mp (EtOAc/light petroleum) 132°-133° C.

Provenance & Evidence