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

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Reaction Steps

To a solution of 100 ml. of water and 120 ml. of tetrahydrofuran is added sequentially 12.4 g. of γ-aminobutyric acid, 10.4 g. of sodium bicarbonate, and 30 g. of N-benzyloxycarbonyloxysuccinimide. The reaction mixture is stirred for approximately 3.5 hours at room temperature and then the tetrahydrofuran is evaporated in vacuo. The residue is diluted with 200 ml. of water and extracted with (2×300 ml.) anhydrous ether. The aqueous layer is then acidified to pH 1-2 with 1 N hydrochloric acid and extracted with (3×400 ml.) methylene chloride. The methylene chloride extracts are collected and combined and then washed with (3×200 ml.) brine solution, dried with anhydrous magnesium sulfate and the solvent evaporated in vacuo at room temperature. The residue provides N-carbobenzoxy-γ-aminobutyric acid.

Provenance & Evidence