2-[(Benzoyloxy)methyl]benzoic acid → Benzamide, 3-methoxy-N,N-bis(1-methylethyl)-

Participants

Reaction Steps

A stirred solution of 4-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide (3.0 g, 7.06 mmol) in 15 mL of dichloromethane is treated with 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (1.67 g, 8.47 mmol), hydroxybenzotriazole (1.14 g, 8.47 mmol), and 2-(benzoyloxymethyl)benzoic acid (1.81 g, 7.06 mmol) and stirred at room temperature over 2 hours. The reaction is concentrated in vacuo and purified by chromatography on silica gel (50 g) with 60% ethyl acetate/hexane as the eluent to afford 4-[5-[4-amino[2-(benzoyloxymethyl)benzoyl]iminomethyl]phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide as a colorless foam:

Provenance & Evidence