Lithium Hydroxide → HCID 72189667, compound

Participants

Reaction Steps

Methyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(1H-imidazol-1-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (Step A, 99 mg, 0.136 mmol) was dissolved in 1,4-dioxane (2.4 mL). Added 0.5N LiOH (1.20 mL, 0.600 mmol), and stirred at room temperature for 2.5 hrs, at which time LCMS indicates the reaction was complete, but not clean. The reaction was quenched with 0.6 mL of 1N HCl, then diluted with pH 7 buffer and extracted twice with ethyl acetate. The organic was washed again with buffer, dried over sodium sulfate filtered and the filtrate evaporated. The crude was taken up in 1.5-2 mL of acetonitrile, and after about 15 minutes white solid came out of solution. The suspension was filtered and a second crystallization set up from the mother liquor. The combined solid recovery was 51 mg of ≧95% pure product. LCMS (M+H)+: 713.1. 1H NMR (CDCl3, 500 MHz): δ 8.75 (br s, 1H), 8.57 (s, 1H), 8.32 (d, 1H), 8.04 (s, 1H), 7.99 (d, 1H), 7.93 (br s, 1H), 7.90 (s, 1H), 7.77 (s, 2H), 7.59 (d, 1H), 7.36 (d, 1H), 7.26 (s, 1H, (under CHCl3)), 5.82 (d, 1H), 4.93 (d, 1H), 4.48 (m, 1H), 4.21 (d, 1H), 4.04 (s, 3H), 2.40 (s, 3H), 0.81 (d, 3H). RTA IC50: 109 nM

Provenance & Evidence