m-Chloroperbenzoic acid → HCID 178520769, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (140 mg, 0.28 mmol) in dichloromethane (DCM) (5 mL) under nitrogen at 0° C. was added 3-chlorobenzenecarboperoxoic acid (147 mg, 0.85 mmol) in one portion. The reaction mixture was stirred at 0° C. for 10 min, then warmed to room temperature and stirred overnight. The reaction mixture was quenched with sat. aq. NaHCO3 and then extracted with DCM. The organics were dried over Na2SO4, filtered, and concentrated to provide the crude product which was purified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-65% MeCN:H2O) to afford (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(5-fluoro-1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (90 mg, 0.18 mmol, 62% yield) as a white solid. MS: 512 ([M]+).

Provenance & Evidence