Hydrogen Peroxide → HCID 11183134, compound

Participants

Reaction Steps

To a 0° C. solution of (4S)-3-[(2S)-2,3-dimethyl-3-phenylbutanoyl]-4-isopropyl-1,3-oxazolidin-2-one (0.13 g, 0.43 mmol, from Reference Example 24) in tetrahydrofuran (6 mL) and water (2 mL) is added 30% aqueous hydrogen peroxide (2.4 mL). After one to two minutes of stirring, lithium hydroxide monohydrate (36 mg) is added and the reaction mixture is allowed to stir overnight while warming to room temperature. On the following day, the reaction mixture is cooled to 0° C. and aqueous sodium sulfite solution (1.5 M, 1.3 mL) is added. After stirring for an hour at room temperature, the reaction mixture is concentrated under reduced pressure. The aqueous residue is extracted twice with dichloromethane, then acidified to pH 1 with 10% aqueous hydrochloric acid solution. The acidified aqueous phase is then extracted thrice with ethyl acetate. The combined organic extracts are washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, decanted, and concentrated under reduced pressure to give a white crystalline solid (60 mg, 72%). Mp 69-72° C. MS (ES−): (M−H)=191.0

Provenance & Evidence