1,2-Dichloroethane → N3-{(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N5,N5-dipropyl[1,1'-biphenyl]-3,5-dicarboxamide hydrochloride

Participants

Reaction Steps

A mixture of 5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylic acid (IX, 188 mg, 0.56 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol dihydrochloride (VIII, Step 2, 230 mg, 0.56 mmol), HOBt (114 mg, 0.84 mmol), and N-methylmorpholine (0.23 g, 2.24 mmol) in methylene chloride (6 mL) and dimethylformamide (1 mL) is stirred at 20–25 degrees C. for 15 minutes EDC (161 mg, 0.84 mmol) is added and the reaction mixture is stirred at 20–25 degrees C. overnight. The reaction mixture is washed with water, 1 N hydrochloric acid, water, and saline, dried (sodium sulfate), and concentrated under reduced pressure to give the title compound, mp 230–233 degrees C.; IR (ATR): 2965, 1651, 1596 and 1267 cm−1; ESI-MS (m/z) [M+H]+=644.

Provenance & Evidence