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

Participants

Reaction Steps

(5S)-1-((2R)-2-(Cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-phenyl-4,5-dihydro-1H-pyrazole-5-carboxamide (110 mg, 0.23 mmol) was dissolved in methanol (8 mL), and Pearlman's catalyst (37 mg, 0.05 mmol) was added. The resulting mixture was stirred under 1 atm of H2 for 30 min. After 30 min, the mixture was filtered, concentrated, and 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-(hydroxyamino)-4-oxobutanoyl]-N-phenyl-4,5-dihydro-1H-pyrazole-5-carboxamide (60 mg, 0.15 mmol, 66% yield) as a white solid. MS: 387 ([M+H]+). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.13 (none, 2H) 1.37-1.68 (m, 5H) 1.72-2.02 (m, 4H) 2.20-2.33 (m, 1H) 2.38-2.50 (m, 1H) 3.05-3.21 (m, 1H) 3.79-3.92 (m, 1H) 7.08-7.15 (m, 2H) 7.28-7.36 (m, 2H) 7.54-7.59 (m, 1H).

Provenance & Evidence