Hydrogen Peroxide → HCID 117389010, compound

Participants

Reaction Steps

(S)-tert-Butyl 3-((R)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-(cyclopropylsulfonyl)phenyl)-3-oxopropyl)pyrrolidine-1-carboxylate (1.38 g, 2.36 mmol) was dissolved in a mixed solvent of tetrahydrofuran and water (3: 1, 12.8 mL), and an aqueous solution (1.9 mL) consisting of lithium hydroxide (113 mg, 4.72 mmol) and a hydrogen peroxide solution (30%, 1.10 mL) was added to the above obtained solution under ice-cold condition. The obtained mixture was stirred for 1 hour. Thereafter, an aqueous solution of sodium sulfite was added to the reaction solution, and the mixed solution was then washed with diethyl ether. The reaction solution was neutralized with a 0.5 M aqueous solution of hydrochloric acid, and was then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated in vacuo, so as to obtain (R)-3-((S)-1-tert-butoxycarbonyl)pyrrolidin-3-yl)-2-(4-(cyclopropylsulfonyl)phenyl)propanoic acid (910 mg, 85%) in the form of a white solid.

Provenance & Evidence