phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl) heptanoyl]-1-pyrazolidinecarboxylate → (3S)-N-(5-fluoro-2-pyridinyl)-2-((2R)-2-{[formyl(hydroxy)amino]methyl}heptanoyl)-3-pyrazolidinecarboxamide

Participants

Reaction Steps

To a 100 mL round-bottomed flask was added phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl) heptanoyl]-1-pyrazolidinecarboxylate (696 mg, 1.123 mmol) in methanol (15 ml), followed by Pearlman's catalyst (120 mg). The mixture was stirred under a balloon of H2 for 80 min. The catalyst was filtered off, and the filtrate was concentrated to dryness to provide (3S)—N-(5-fluoro-2-pyridinyl)-2-((2R)-2-{[formyl(hydroxy)amino]methyl}heptanoyl)-3-pyrazolidinecarboxamide as a colorless oil. (420 mg, 94%). LCMS: (M+H)+: 396.0. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.75-1.00 (m, 3H) 1.16-1.39 (m, 6H) 1.47 (dd, J=8.59, 5.56 Hz, 1H) 1.52-1.68 (m, 1H) 2.02-2.31 (m, 1H) 2.49 (ddd, J=12.06, 6.25, 2.65 Hz, 1H) 2.86 (td, J=10.48, 6.06 Hz, 1H) 3.36 (br. s., 1H) 3.39-3.55 (m, 1H) 3.59-3.89 (m, 2H) 4.54-4.72 (m, 1H) 7.53 (ddd, J=9.16, 7.89, 3.16 Hz, 1H) 7.83 (s, 1H) 8.03-8.20 (m, 2H).

Provenance & Evidence