Lithium hydroxide, monohydrate → HCID 71603339, compound

Participants

Reaction Steps

To a solution of {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (97 mg, 0.193 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (92.4 mg, 2.2 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred for four hours under a nitrogen atmosphere. The solvent was evaporated. Water (˜25 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (3.9 mL). The resulting white precipitate was collected by filtration, washed with water and hexanes, and dried under high vacuum to provide {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (65.8 mg, 70%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.50 (br. s, 1H), 8.97 (br. s, 1H), 8.00-8.22 (m, 1H), 7.97 (s, 1H), 7.90 (dd, J=9.10, 6.50 Hz, 1H), 7.78 (d, J=8.50 Hz, 1H), 7.66-7.73 (m, 1H), 7.49 (t, J=8.30 Hz, 1H), 7.30-7.38 (m, 1H), 7.28 (d, J=8.30 Hz, 1H), 4.28-4.36 (m, 2H), 3.71-3.85 (m, 3H), 3.01-3.18 (m, 2H), 2.43 (s, 3H), 2.17-2.34 (m, 1H), 1.64-1.73 (m, 2H). MS cald. for C26H25F4N2O3 [(M+H)+]: 489, obsd. 489.2.

Provenance & Evidence