Lithium Hydroxide → HCID 72189372, 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-(morpholin-4-yl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (Step A, 200 mg, 0.268 mmol) was dissolved in 1,4-dioxane (5.0 mL). Lithium hydroxide (0.5M, 2.4 mL, 1.20 mmol) was added, and the reaction was stirred at room temperature for 2 hours. The reaction was quenched by adding 1.20 mL of 1N HCl, followed by water. The aqueous reaction mixture was extracted with ethyl acetate, then dried over sodium sulfate, filtered and evaporated. Purified on BIOTAGE SNAP C18 column, eluting with 40-100% CH3CN/water (0.05% TFA) and recovering purified fractions by partitioning them between pH 7 phosphate buffer and ethyl acetate. Extracted the aqueous a second time with ethyl acetate, then washed the combined organics with pH 7.0 buffer and brine. The organic was dried over sodium sulfate, filtered and evaporated to give the titled compound. LCMS (M+H)+: 732.5. 1H NMR (CDCl3, 500 MHz): δ 8.22 (d, 1H), 8.20 (s, 1H), 8.03 (s, 1H), 7.99 (d, 1H), 7.88 (s, 1H), 7.72 (s, 2H), 7.48 (d, 1H), 7.35 (d, 1H), 5.64 (d, 1H), 4.76 (d, 1H), 4.32 (m, 1H), 4.00 (m, s, 4H), 3.86 (m, 4H), 3.81 (m, 4H), 2.39 (s, 3H), 0.72 (d, 3H). RTA IC50: 13 nM.

Provenance & Evidence