Benzoic Acid → Ethyl Hippurate

Participants

Reaction Steps

DIPEA (0.425 mL, 2.46 mmol) was added to a stirred solution of benzoic acid (100 mg, 0.82 mmol) in DMF (2 mL). HOBT (132 mg, 0.98 mmol) and EDCI.HCl (188 mg, 0.98) were then added, followed by the addition of ethyl glycine ester hydrochloride (0.82 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (using silica gel, 60-120 A° and 20% methanol in chloroform as the eluent) afforded Benzoylamino-acetic acid ethyl ester in 53% yield, LC-MS purity: 98%

Provenance & Evidence