(5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-4-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide → (5S)-1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-4-pyrimidinyl-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-4-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide (76 mg, 0.159 mmol) and Pearlman's catalyst (22.30 mg, 0.032 mmol) in methanol (8.8 ml) was degassed and placed under 1 atm of H2 at ambient temperature. After 1 h 50 min, 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-4-pyrimidinyl-4,5-dihydro-1H-pyrazole-5-carboxamide (58 mg, 0.148 mmol, 93% yield). MS (ES+) m/z 389.2 (MH+). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.04-1.21 (m, 2H) 1.37-1.67 (m, 5H) 1.70-1.99 (m, 4H) 3.05-3.20 (m, 1H) 3.35 (d, J=11.87 Hz, 1H) 3.55 (dd, J=14.02, 4.67 Hz, 1H) 3.75-3.90 (m, 1H) 3.90-4.02 (m, 1H) 4.99 (dd, J=11.87, 5.81 Hz, 1H) 7.11 (s, 1H) 7.89 (s, 0.7H) 8.14 (d, J=5.31 Hz, 1H) 8.22 (s, 0.3H) 8.60 (d, J=5.81 Hz, 1H) 8.83 (s, 1H)

Provenance & Evidence