HCID 178520769, compound → HCID 178520768, compound

Participants

Reaction Steps

(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) was dissolved in methanol (8 mL), and Pearlman's catalyst (24 mg, 0.03 mmol) was added to the solution. The mixture was stirred under 1 atm of H2 (balloon) for 1 hour. After 1 hour, the reaction 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-(5-fluoro-1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (38 mg, 0.09 mmol, 50% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.79-0.94 (m, 1H) 1.04-1.24 (m, 3H) 1.41-1.68 (m, 7H) 1.72-2.32 (m, 18H) 2.39-2.52 (m, 2H) 2.58-2.74 (m, 2H) 3.21-3.31 (m, 1H) 3.39-3.50 (m, 1H) 3.69-3.81 (m, 1H) 5.08-5.22 (m, 1H) 7.03-7.07 (m, 1H) 7.17-7.24 (m, 2H) 8.23-8.29 (m, 1H) 8.42-8.49 (m, 1H) 10.92-11.05 (m, 1H). MS: 422 ([M+H]+).

Provenance & Evidence