Hydrogen Peroxide → (2S,3S)-2-Azido-3-(4-fluorophenyl)butanoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product from Step C (0.88 g, 2.39 mmol) in THF (30 mL) was added water (10 mL). The solution was stirred at 0° C. for 15 min, and then 30% hydrogen peroxide (1.60 mL, 14.3 mmol) was added followed by slow addition of lithium hydroxide (0.17 g, 7.23 mmol). The resultant mixture was stirred at 0° C. for 4 h. The reaction was quenched by addition of saturated aqueous sodium sulfite solution and stirred at room temperature for 30 min. The aqueous phase was separated and extracted with three portions of dichloromethane. The aqueous phase was then acidified to pH 1 with 3N hydrochloric acid and extracted with three portions of ethyl acetate. The ethyl acetate extracts were combined, dried over sodium sulfate, and evaporated in vacuo to give the product, which was used in the next step directly. LC/MS 224.1 (M+1).

Provenance & Evidence