Water → (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-(5-isopropyl-2-methoxypyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Potassium peroxymonosulfate (4.08 g, 6.63 mmol) was added to an acetonitrile (12 mL) and water (8 mL) suspension of title compound from step A above (1.66 g, 2.76 mmol). This was then stirred for 2 hours at 25° C., at which time LCMS showed complete conversion to product. The reaction was diluted with methyl t-butyl ether (50 mL) and poured into water (100 mL). The organic layer was washed twice with 100 mL aqueous NaCl, then dried over sodium sulfate, filtered and the filtrate concentrated to give a white solid, which can be used without further purification. LCMS (M+H)+: 633.4. 1H NMR (CDCl3, 500 MHz) δ 8.75 (s, 1H), 8.24 (d, J=2.2 Hz, 1H), 7.92 (s, 1H), 7.80 (s, 2H), 7.49 (d, J=2.2 Hz, 1H), 5.89 (d, J=8.3 Hz, 1H), 4.93 (d, J=17.7 Hz, 1H), 4.59 (m, 1H), 4.26 (d, J=17.7 Hz, 1H), 3.98 (s, 3H), 3.43 (s, 3H), 3.02 (m, 1H), 1.33 (d, J=6.9 Hz, 6H), 0.80 (d, J=6.6 Hz, 3H).

Provenance & Evidence