HCID 86706349, compound → HCID 66547913, compound

Participants

Reaction Steps

To a solution of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(5-methyl-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate (combined from Part A, Batches 1 and 2, 142 mg, 0.226 mmol) in methanol (6 ml) was added 20% palladium hydroxide on carbon (70 mg, 0.226 mmol). The mixture was hydrogenated under balloon pressure for 1 h 30 min. and then filtered. The mixture was purified by reverse-phase HPLC to yield (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-methyl-2-pyridinyl)-3-pyrazolidine carboxamide (68 mg, 0.170 mmol, 75% yield). LC/MS: (M+H)+: 404.0. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.06-1.26 (m, 2H) 1.35-1.48 (m, 1H) 1.48-1.69 (m, 4H) 1.69-1.99 (m, 4H) 2.17-2.31 (m, 3H) 2.45-2.64 (m, 1H) 2.80-3.01 (m, 1H) 3.16-3.31 (m, 1H) 3.51 (dd, J=14.02, 4.42 Hz, 1H) 3.66-3.84 (m, 2H) 3.95 (dt, J=9.35, 4.67 Hz, 1H) 4.70 (td, J=7.96, 4.04 Hz, 1H) 7.61 (dd, J=8.08, 2.02 Hz, 1H) 7.88 (s, 1H) 7.98 (d, J=8.34 Hz, 1H) 8.13 (d, J=2.27 Hz, 1H).

Provenance & Evidence