(5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide → (5S)-1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Participants

Reaction Steps

A mixture of (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (104 mg, 0.210 mmol) and Pearlman's catalyst (29.5 mg, 0.042 mmol) in methanol (12.3 ml) was degassed and placed under 1 atm of H2 at ambient temperature. After 2 hrs, the reaction mixture was filtered and concentrated to give a residue which was purified by RP-HPLC to give (5S)-1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (71 mg, 0.173 mmol, 83% yield). MS (ES+) m/z 406.1 (MH+) 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.12 (dq, J=11.78, 8.12 Hz, 2H) 1.37-1.67 (m, 5H) 1.70-1.99 (m, 4H) 3.05-3.19 (m, 1H) 3.27 (s, 1H) 3.54 (dd, J=14.15, 4.55 Hz, 1H) 3.75-3.89 (m, 1H) 3.89-4.03 (m, 1H) 4.97 (dd, J=11.87, 5.81 Hz, 1H) 7.11 (s, 1H) 7.50-7.62 (m, 1H) 7.89 (s, 0.7H) 8.12 (dd, J=9.09, 4.04 Hz, 1H) 8.18 (d, J=3.03 Hz, 1H) 8.22 (s, 0.3H)

Provenance & Evidence