Lithium hydroxide, monohydrate → HCID 71604237, compound

Participants

Reaction Steps

To a solution of {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (104.2 mg, 0.199 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (95.3 mg, 2.3 mmol) in water (2 mL). The reaction mixture was stirred at room temperature overnight under nitrogen. After this time, the reaction mixture was concentrated. Water (˜25 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (4 mL). The resulting white precipitate was collected by vacuum filtration, washed with water and hexanes, and then further dried under vacuum to afford {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (92.2 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (br. s, 1H), 8.18-8.20 (m, 1H), 8.16-8.18 (m, 1H), 8.07 (s, 1H), 7.97 (t, J=7.80 Hz, 1H), 7.84-7.91 (m, 1H), 7.67 (s, 1H), 7.33 (t, J=9.00 Hz, 1H), 3.92 (br. s., 2H), 3.74 (s, 2H), 3.41-3.70 (m, 2H), 2.57-2.84 (m, 2H), 2.31 (s, 3H), 2.40-2.28 (m, 1H), 1.69 (m, 2H). MS cald. for C25H22F4NO4S [(M−H)−]: 508, obsd. 508.1.

Provenance & Evidence