Water → 1-(2,3-dihydroxypropyl)-N-(4-fluoro-5-((4-bromo-2-chloro phenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide

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Reaction Steps

To a solution of 1-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide (100 mg, 0.38 mmol) in THF (10 mL) was added N-methylmorpholine-N-oxide (44 mg, 0.38 mmol) followed by osmium tetraoxide (10 mg, 0.04 mmol) and water (0.5 mL). After stirring at room temperature overnight, the mixture was concentrated and then diluted with EA. The organic layer was washed with water, saturated NaHCO3 (aq.) and brine sequentially, dried over Na2SO4, filtered and concentrated to give a residue, which was purified by flash chromatography to give the product as white solid (30 mg, 28.2% yield). 1H NMR (400 MHz, CDCl3): δ 8.10 (s, 1H), 7.98 (s, 1H), 7.45-7.34 (m, 2H), 7.32-7.21 (m, 1H), 6.83 (s, 1H), 6.44-6.30 (m, 1H), 4.41-4.25 (m, 2H), 4.21-4.12 (m, 1H), 3.72-3.62 (m, 1H), 2.85-2.78 (m, 1H), 1.32-1.26 (m, 2H), 1.16-1.21 (m, 4H). MS APCI (+) m/z: 535.8, [M+H].

Provenance & Evidence