tert-Butyl methyl ether → 4-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfonyl)pyrimidin-5-yl]-4-tert-butyl-1,3-thiazol-2-yl}-3-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

4-{5-[4-({(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfanyl)pyrimidin-5-yl]-4-tert-butyl-1,3-thiazol-2-yl}-3-methylbenzoic acid (INTERMEDIATE 51, 225 mg, 0.31 mmol) was dissolved in 10 mL CH3CN and 10 mL of water. Potassium peroxymonosulfate (5.1 g, 8.31 mmol) was added, and it was stirred at 60° C. for 2 hours. Then, it was worked up with water (100 mL) and t-butyl methyl ether (200 mL). The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated. The crude isolate was purified by silica gel chromatography, eluting with 60% ethyl acetate in hexanes to give the title compound as a slightly yellow solid (226 mg, 96% yield). LCMS (M+H)+: 757.1 1H NMR (DMSO, 500 MHz): δ 9.24 (s, 1H), 8.15 (s, 1H), 8.03 (s, 2H), 7.96 (s, 1H), 7.90 (s, 2H), 6.06 (m, 1H), 4.48 (m, 1H), 3.52 (s, 3H), 2.69 (s, 3H), 1.26 (s, 9H), 0.72 (d, J=6.0 Hz, 3H).

Provenance & Evidence