Hydrogen Peroxide → 2-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid

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Reaction Steps

Hydrogen peroxide (0.37 ml, 27.5 wt % in water) was added to an ice-cold solution of 4-(R)-Benzyl-3-(2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one(0.67 g) in tetrahydrofuran (5 ml), followed by the dropwise addition of a solution of lithium hydroxide monohydrate (61 mg) in water (2.5 ml), and the mixture stirred in the ice-bath, allowing to slowly warm to ambient temperature. After 4 h, the mixture was re-cooled in ice, treated with sodium sulfite (0.68 g) as a solution in water (15 ml), and stirred for 10 min. The mixture was then reduced in vacuo and the residue diluted with 1 M sodium hydroxide (10 ml) and washed with ethyl acetate (2×30 ml). The combined organic washes were back-extracted with 1M sodium hydroxide (2×10 ml), and the combined aqueous phase was acidified with citric acid to pH 3-4. The resultant suspension was filtered, and the solids washed with water and dried under vacuum at 40° C. to yield the title compound as a white solid (0.36 g, 74%).

Provenance & Evidence