Lithium Hydroxide → HCID 71604240, compound

Participants

Reaction Steps

To a light yellow solution of {6-fluoro-3-methyl-4-[1-(2-nitro-phenylmethanesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (100 mg, 0.194 mmol) in THF (4 mL) was added a solution of lithium hydroxide (93.1 mg, 3.89 mmol) in water (1 mL) at room temperature. The resulting light brown solution was stirred for 15 hours at room temperature. The THF was evaporated off under vacuum and the basic aqueous layer was neutralized with 1.0 N HCl. The resulting solids were filtered using filter paper and washed with water and hexanes. The white solid (82 mg) was dissolved in ethyl acetate (˜5 mL) with heating and the mixture was diluted with hexanes. During the dilution some precipitate was formed. Cooling in the refrigerator precipitated additional solids. {6-Fluoro-3-methyl-4-[1-(2-nitro-phenylmethanesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (88 mg, 90%) was isolated as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.44 (br. s, 1H), 8.08 (d, J=8.03 Hz, 1H), 7.90 (dd, J=8.91, 6.65 Hz, 1H), 7.74-7.86 (m, 3H), 7.64-7.73 (m, 2H), 7.36 (t, J=8.03 Hz, 1H), 4.97 (s, 2H), 3.52-3.90 (m, 7H), 2.42 (br. s, 3H), 1.60-184 (m, 4H). MS cald. for C25H25FN2O6S [(M+H)+] 500, obsd. 501.1.

Provenance & Evidence