1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-L-prolinamide → 1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-L-prolinamide

Participants

Reaction Steps

1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-L-prolinamide (24 g, 0.060 mol) was dissolved in MeOH (500 mL) and degassed. Catalyst (10% Pd/C, Degussa type, wet, 2.4 g) was added and the mixture was stirred under a hydrogen balloon for 3 hours. After degassing, the suspension was filtered through Celite, washing with methanol, and the filtrate was concentrated. The resulting foam was dissolved in ethyl acetate (50 mL) and diluted with toluene (˜500 mL.) This solution was then concentrated to a slurry (˜100 mL) and diluted with hexanes (200 mL.) Filtration, washing with hexanes and drying afforded the product 1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-L-prolinamide (21 g, 113% yield). The excess yield is due to residual toluene. LC/MS m/z 312 (MH+)

Provenance & Evidence