Water → 4-(2-(1,2-dihydroxyethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Participants

Reaction Steps

To a solution of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-4-(2-vinylphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (750 mg, 1.445 mmol) in t-BuOH (10 mL) and water (5 mL) was added NMO (338 mg, 2.890 mmol, Aldrich) followed by OsO4 (4% in water) (0.7 mL, 0.144 mmol, Aldrich) at 0° C. The reaction mixture was stirred at ambient temperature for 12 h. After completion, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 mL) and extracted with DCM (2×10 mL). The organic layer was dried over sodium sulfate and concentrated reduced pressure to obtain crude 4-(2-(1,2-dihydroxyethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 37.5%) which was used in the next step without purification. m/z (ESI) 553.9 (M+H)+.

Provenance & Evidence