Lithium Hydroxide → HCID 72190295, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4-{5-[2-(3-fluoroazetidin-1-yl)-4-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzoate (Step A, 82 mg, 0.118 mmol) in dioxane (2.4 mL) was added an aqueous solution of lithium hydroxide (1.2 mL, 0.5 M). The mixture was heated at 60° C. for one hour. The reaction mixture was cooled and acidified by the addition of TFA (0.090 mL, 1.17 mmol). Volatiles were removed under reduced pressure and the residue was purified by preparative HPLC reverse phase (C-18) to give 4-{5-[2-(3-fluoroazetidin-1-yl)-4-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3,5-dimethylbenzoic acid (60.7 mg, 0.089 mmol) as a white solid following lyophilization. LCMS (M+H)+: 684.1. 1H NMR (500 MHz, CD3OD): δ 8.19 (s, 1H), 8.03 (s, 1H), 7.80 (s, 2H), 7.50 (m, 3H), 7.40 (m, 1H), 5.80 (d, 1H, J=8.4 Hz), 5.49 (br s, 0.5H), 5.42 (br s, 0.5H), 4.64 (d, 1H, J=16.9 Hz), 4.50 (m, 2H), 4.40 (m, 1H), 4.24 (m, 2H), 4.14 (d, 1H, J=16.9 Hz), 4.02 (s, 3H) 2.17 (s, 3H), 2.16 (s, 3H), 0.76 (d, 3H, J=6.6 Hz). RTA IC50: 15 nM.

Provenance & Evidence