Formic Acid → (R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acid

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, formic acid (192 mL, 5 mol) was dissolved in CH2Cl2 (450 mL) and cooled to 0° C. Acetic anhydride (73 mL, 0.77 mol) was then added, and the reaction mixture was stirred for 45 min. After this time, a solution of (2R)-3-cyclopentyl-2-({[(phenylmethyl)oxy]amino}methyl)propanoic acid (22.85 g crude material, assumed 77.1 mmol) in CH2Cl2 (450 mL) was added, and the resulting mixture was stirred for 1.5 h at 0° C. The volatiles were then removed, the crude residue was dissolved in EtOAc (500 mL), and the mixture was washed with brine (4×100 mL). The organics were dried (MgSO4) and concentrated to provide (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (23.5 g, 100%) as a thick syrup. LCMS: (M+H)+: 306.1.

Provenance & Evidence