Benzyl chloroformate → (2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid

Participants

Reaction Conditions

Reaction Steps

10 g of 2(S)-aminobutyric acid (97 mmol) are dissolved in aqueous 4M KOH solution (100 ml) and the mixture is cooled to 0° C. 24.7 g of benzyl chloroformate (145 mmol) are added and the mixture is stirred while allowing its temperature to rise to room temperature over 2 hours 30 minutes. The mixture is then diluted with water (100 ml) and extracted with ether (2×200 ml). The aqueous phase is acidified to a pH<1 with concentrated HCl and is extracted with ethyl acetate (3×200 ml). The ethyl acetate fractions are combined and dried (Na2SO4) and the solvent is removed. A white solid is obtained.

Provenance & Evidence