m-Chloroperbenzoic acid → HCID 15605226, compound

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Reaction Steps

3-chloroperoxybenzoic acid (28 mg, 1.5 eq) was added to a solution of the diastereomer mixture of the alcohols from Examples 75 and 76 in chloroform (3 mL) at room temperature. After 3 h, the mixture was quenched with saturated NaHCO3 (1 mL), diluted with EtOAc (60 mL), washed with water (5 mL), brine (5 mL), dried (MgSO4) and concentrated. Reverse phase HPLC purification (MeOH-water, 50 to 100%) yielded the desired N-oxide as a mixture of two diastereomers (5 mg), which was separated by chiral OD column (isocratic, i-PrOH/heptane, 15%) to give Examples 78 (1.3 mg, 3%, isomer A, faster eluent) and 79 (1.5 mg, 4%, isomer B, slower eluent). MS found: (M+H)+=380.

Provenance & Evidence