m-Chloroperbenzoic acid → HCID 178436409, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(6-ethyl-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (119 mg, 0.24 mmol) in dichloromethane (DCM) (5 mL) stirred under nitrogen at 0° C. was added 3-chlorobenzenecarboperoxoic acid (122 mg, 0.71 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 then quenched with sat. aq. NaHCO3 and extracted with DCM. The organic phase was 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-(6-ethyl-1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (61 mg, 0.12 mmol, 50% yield) as a white solid. MS: 522 ([M+H]+).

Provenance & Evidence