Gamma-Aminobutyric Acid → 4-(((Tert-butoxy)carbonyl)amino)butanoic acid

Participants

Reaction Steps

To a solution of γ-aminobutyric acid (1 equivalent) in t-BuOH (4 ml/gram) and H2O (3 ml/gram) was added NaOH (1 equivalent), BOC2O (1 equivalent), and the mixture was stirred at room temperature for 24 hours. The solvent was thereafter evaporated and the residue was partitioned between hexane and water. The aqueous layer was acidified with KHSO41N to reach pH=2, and was thereafter extracted with CH2Cl2. The organic layer was dried over MgSO4 and the solvent was evaporated to give the desired product as a white solid (85% yield).

Provenance & Evidence