Tert-Butyl nitrite → (S)-2-Acetoxybutanoic acid

Participants

Reaction Conditions

Reaction Steps

Sodium acetate (11.9 g, 146 mmol) and tert-butyl nitrite (15.0 g, 146 mmol) were added to an acetic acid (300 mL) solution of (2S)-2-aminobutyric acid (10.0 g, 97.0 mmol) under ice cooling, and was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was subjected to extraction twice with ethyl acetate. The organic layer thus obtained was washed with water and brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, further the residue was azeotropically boiled with 1,4-dioxane (50 mL) twice. Thus, the title compound (8.4 g, yield: 60%) was obtained.

Provenance & Evidence