(1,1'-Biphenyl)-4-carboxylic acid → Ethyl 2-[(4-phenylphenyl)carbonylamino]acetate

Participants

Reaction Steps

DIPEA (7.825 g, 60.54 mmol) was added to a stirred solution of biphenyl-4-carboxylic acid (4 g, 20.18 mmol) in DMF (40 mL). HOBT (3.27 g, 24.22 mmol) and EDCI.HCl (3.87 mg, 24.22 mmol) were then added at room temperature. After 2 minutes, glycine ethyl ester hydrochloride (3.381 g, 24.22 mmol) was added and the resulting mixture was stirred overnight. The reaction mixture was diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 5 g (87.4% yield) of [(biphenyl-4-carbonyl)-amino]-acetic acid ethyl ester. LC-MS purity: 93.4%

Provenance & Evidence