Phenylmethyl (3S)-3-{[(6-chloro-2-pyridinyl)amino]carbonyl}-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-pyrazolidinecarboxylate → (3S)-N-(6-chloro-2-pyridinyl)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinecarboxamide

関与物質

反応手順

To a solution of phenylmethyl (3S)-3-{[(6-chloro-2-pyridinyl)amino]carbonyl}-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-pyrazolidinecarboxylate (268 mg, 0.413 mmol) in methanol (8 ml) was added 20% palladium hydroxide on carbon (80 mg, 0.413 mmol). The mixture was hydrogenated under balloon pressure for 1 h 20 min. and then filtered. The filtrate was purified by reverse-phase HPLC to yield (3S)—N-(6-chloro-2-pyridinyl)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinecarboxamide (55 mg, 0.129 mmol, 31% yield). LC/MS: (M+H)+: 423.9. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.06-1.31 (m, 2H) 1.31-1.47 (m, 1H) 1.47-1.69 (m, 4H) 1.69-1.98 (m, 4H) 2.11-2.37 (m, 1H) 2.40-2.66 (m, 1H) 2.79-3.01 (m, 1H) 3.17-3.31 (m, 1H) 3.51 (dd, J=14.15, 4.55 Hz, 1H) 3.61-3.85 (m, 2H) 3.95 (td, J=9.54, 4.93 Hz, 1H) 4.60-4.76 (m, 1H) 7.14 (d, J=7.83 Hz, 1H) 7.75 (t, J=7.96 Hz, 1H) 7.88 (s, 1H) 8.08 (d, J=8.08 Hz, 1H).

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