Lithium hydroxide, monohydrate → 2-Dibenzylamino-3-hydroxy-4-phenyl-butyric acid

Participants

Reaction Conditions

Reaction Steps

To 5.43 g (13.5 mmol) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-4-phenyl-butyric acid ethyl ester in 75 ml tetrahydrofurane were added 2.28 g (53.8 mmol) lithium hydroxide monohydrate dissolved in 13.5 ml water. The mixture was stirred at 60° C. overnight. Water was added followed by extraction with ethyl acetate. The waterphase was adjusted to pH 1 with 1 N aqueous hydrochloric acid. Extraction with ethylacetate and chromatography on silicagel with dichloromethane/methanol 9/1 yielded 3.50 g (69%) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-4-phenyl-butyric acid, MS m/e (%): 376.5 (M+H+, 100).

Provenance & Evidence