m-Chloroperbenzoic acid → HCID 22022962, compound

Participants

Reaction Steps

To a stirred solution of (5RS)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (174 mg, 0.48 mM) in dichloromethane (5 ml) was added dropwise a solution of 3-chloroperoxybenzoic acid (80%, 124 mg, 0.57 mM) in dichloromethane (5 ml) at ambient temperature, and stirring continued for 1 hour. Aqueous sodium metabisulfite (5%, 5 ml) was added, and after stirring for 5 minutes the organic phase was separated. After further extraction with dichloromethane (2×10 ml), the combined extracts were washed with aqueous sodium bicarbonate solution (2×15 ml) and dried (magnesium sulfate). Crude product was chromatographed on a 10 g silica Mega Bond Elut® column, eluting first with a gradient from 0–50% ethyl acetate in dichloromethane (to remove sulfone, 10 mg), then with a gradient from 0–2.5% methanol in dichloromethane. Relevant fractions were combined to give the desired product (128 mg).

Provenance & Evidence