Reaktion #1484058

Reaktionsgleichung

phenylmethyl 2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(5-fluoro-1-oxido-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate

→

(3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-fluoro-1-oxido-2-pyridinyl)-3-pyrazolidinecarboxamide

Ausbeute 18.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   SonstigeThe filtrate was purified by reverse-phase HPLC

Vorschrift

To a solution of phenylmethyl 2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(5-fluoro-1-oxido-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate (104 mg, 0.161 mmol) in methanol (4 ml) was added 20% palladium hydroxide on carbon (50 mg, 0.161 mmol). The mixture was hydrogenated under balloon pressure for 1 h and then filtered. The filtrate was purified by reverse-phase HPLC to yield (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-fluoro-1-oxido-2-pyridinyl)-3-pyrazolidinecarboxamide (13 mg, 0.028 mmol, 18% yield). LC/MS: (M+H)+: 423.8. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.00-1.27 (m, 2H) 1.39-1.69 (m, 5H) 1.70-1.99 (m, 4H) 2.25-2.45 (m, 1H) 2.45-2.64 (m, 1H) 2.84-3.03 (m, 1H) 3.18-3.30 (m, 1H) 3.53 (dd, J=14.02, 4.42 Hz, 1H) 3.74-3.88 (m, 1H) 3.98 (td, J=9.28, 4.93 Hz, 1H) 4.74-4.87 (m, 1H) 7.37-7.54 (m, 1H) 7.89 (s, 1H) 8.37-8.60 (m, 2H).

Quelle