Lithium Hydroxide → HCID 72189669, compound

Participants

Reaction Steps

Methyl 4-{5-[4-{[(4S,5R)-5-(3,5-difluorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-2-(3-fluoroazetidin-1-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (Step A, 65 mg, 0.103 mmol) was dissolved in 1,4-dioxane (2 mL). Added 0.5N lithium hydroxide (1.0 mL, 0.50 mmol) and stirred at room temperature for 2.5 hours at which time LCMS shows complete hydrolysis. The reaction was quenched by adding 0.50 mL of 1N HCl, followed by water. The reaction was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered and evaporated. The crude isolate was purified on a BIOTAGE SNAP C18 column, eluting with 40-100% CH3CN/water (0.05% TFA). The purified fractions were partitioned between pH 7 phosphate buffer and ethyl acetate. The aqueous was extracted a second time with ethyl acetate, then washed with pH 7.0 buffer and brine. The organic was dried over sodium sulfate, filtered and evaporated to give the title compound. LCMS (M+H)+: 620.2. 1H NMR (CDCl3, 500 MHz): δ 8.21 (br, 1H), 8.20 (s, 1H), 8.02 (s, 1H), 7.97 (d, 1H), 7.47 (s, 1H), 7.33 (d, 1H), 6.81 (m, 3H), 5.50 (d, 1.5H), 5.40 (m, 0.5H), 4.69 (d, 1H), 4.47 (m, 2H), 4.33 (m, 3H), 4.00 (d, s, 4H), 2.38 (s, 3H), 0.76 (d, 3H). RTA IC50: 35 nM

Provenance & Evidence