Diethyl Ether → (R)-2-(((Benzyloxy)carbonyl)amino)-3-mercapto-3-methylbutanoic acid

Participants

Reaction Conditions

Reaction Steps

To L-penicillamine (15.75 g; 105.8 mmol) was added a solution of KOH (12.4 g; 222.2 mmol) in water (250 ml). When the solution was complete, Et2O (100 ml) was added and the solution cooled to 0° C. Benzyl chloroformate (14.9 ml; 105.8 mmol) was added dropwise and the stirred reaction mixture allowed to warm to RT. The layers were separated, the aqueous layer acidified to pH 1-1.5 with 1N hydrochloric acid, extracted with CH2Cl2 (×3) and dried (MgSO4). The solvent was removed in vacuo to yield N-benzyloxycarbonyl-L-penicillamine (21.27 g).

Provenance & Evidence