1,2-Dichloroethane → (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-phenyl-4,5-dihydro-1H-pyrazole-5-carboxamide

Participants

Reaction Steps

To a solution of (3R)-3-(cyclopentylmethyl)-4-oxo-4-{5-[(phenylamino)carbonyl]-4,5-dihydro-1H-pyrazol-1-yl}butanoic acid (336 mg, 0.90 mmol) in dichloromethane (DCM) (10 ml) was added O-(phenylmethyl)hydroxylamine (167 mg, 1.36 mmol), 4-methylmorpholine (0.26 ml, 2.35 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (123 mg, 0.90 mmol), and EDC (208 mg, 1.09 mmol) at 0° C. The reaction was left to warm to room temperature and stirred overnight. The reaction was washed with water (15 mL) and NaHCO3 solution (15 mL×3), and then concentrated to give the crude product as a mixture of diastereomers, which was purified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-65% MeCN:H2) to afford (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-phenyl-4,5-dihydro-1H-pyrazole-5-carboxamide (110 mg, 25% yield). MS: 477 ([M+H]).

Provenance & Evidence