Water → alpha-Benzyl-alpha-benzyloxycarbonylamino-gamma-butyrolactone

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Reaction Steps

To a stirred solution of 1.55 g of α-benzyl-α-amino-γ-butyrolactone in 16 ml of tetrahydrofuran is added 2.0 g of powdered sodium carbonate, followed by 1.27 ml of benzylchloroformate. After stirring at room temperature for 18 hours, water is added to dissolve the salt and the resulting mixture is diluted with 100 ml of ethyl acetate. It is washed with 50 ml of saturated aqueous sodium chloride. The aqueous phase is extracted with two 50 ml portions of ethyl acetate. The combined organic phase is dried (magnesium sulfate), filtered, and then concentrated. The residue is passed through 20 g of silica gel with ethyl acetate, and the filtrate concentrated to the title product as a white solid, 2.6 g.

Provenance & Evidence