phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[(4-pyrimidinylamino)carbonyl]-1-pyrazolidinecarboxylate → (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-4-pyrimidinyl-3-pyrazolidinecarboxamide

Participants

Reaction Steps

A mixture of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[(4-pyrimidinylamino)carbonyl]-1-pyrazolidinecarboxylate (1.21 g, 1.96 mmol) and Pearlman's catalyst (0.276 g, 0.39 mmol) in methanol (109 ml) was degassed and placed under 1 atm of H2 at 25° C. After 2 hrs, the reaction mixture was filtered and concentrated. Purification by reverse phase HPLC (Gilson) provided (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-4-pyrimidinyl-3-pyrazolidinecarboxamide (554 mg, 70% yield).

Provenance & Evidence