Hydrogen Peroxide → HCID 66845563, compound

Participants

Reaction Steps

Lithium hydroxide hydrate (0.22 g, 5.24 mmol) was dissolved in THF (20 mL) and water (10 mL) and then treated with hydrogen peroxide (35 wt %) (1.00 g, 10.3 mmol). After stirring at ambient temperature for 30 minutes, the solution was cooled to 0° C. (S)-tert-Butyl 2-((S)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-2-oxoethyl)pyrrolidine-1-carboxylate (1.44 g, 2.62 mmol) was added as a solution in THF (10 mL). The mixture was stirred at 0° C. for 1 hour and then warmed to ambient temperature overnight. The reaction was quenched with 10% K2SO3 (4 mL) and saturated NaHCO3 (4 mL) and stirred at ambient temperature for 20 minutes. The reaction was concentrated in vacuo, and the aqueous phase was washed with ether (3×50 mL). The aqueous phase was diluted with ethyl acetate (50 mL), cooled to 0° C., and acidified with 1N HCl to a pH of 3. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with 1N HCl (2×20 mL), dried over Na2SO4 and then concentrated in vacuo (0.036 g, 3.52% yield). MS (APCI−) [M−H] 389.8.

Provenance & Evidence