(5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(6-ethyl-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide → (5S)-1-[(2R)-2-(cyclopentylmethyl)-4-(hydroxyamino)-4-oxobutanoyl]-N-(6-ethyl-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Participants

Reaction Steps

(5S)-1-((2R)-2-(Cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(6-ethyl-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (157 mg, 0.31 mmol) was dissolved in methanol (8 mL), and Pearlman's catalyst (43 mg, 0.06 mmol) was added to the solution. The mixture was stirred under 1 atm of H2 for 4 hours. After 4 hours, the reaction mixture was filtered, and the filtrate was 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-(6-ethyl-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (62 mg, 0.14 mmol, 45% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.14 (m, J=5.81 Hz, 1H) 1.29 (t, J=7.58 Hz, 3H) 1.39-1.68 (m, 5H) 1.70-1.97 (m, 4H) 2.27 (dd, J=14.53, 6.19 Hz, 1H) 2.47 (dd, J=14.40, 9.09 Hz, 1H) 2.76 (q, J=7.66 Hz, 2H) 3.17 (m, J=5.68, 1.89 Hz, 1H) 3.87 (tt, J=8.62, 6.03 Hz, 1H) 5.00 (dd, J=11.12, 5.05 Hz, 1H) 7.04 (d, J=7.58 Hz, 1H) 7.12 (s, 1H) 7.72 (t, J=7.83 Hz, 1H) 7.87 (d, J=8.59 Hz, 1H). MS: 417 ([M+H]+).

Provenance & Evidence