Lithium hydroxide, monohydrate → HCID 71604176, compound

Participants

Reaction Steps

To a solution {4-[1-(3-chloro-phenylmethanesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (52.4 mg, 0.104 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (49.8 mg, 2.08 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred overnight under a nitrogen atmosphere. The solvent was evaporated. Water (˜25 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (2.1 mL). The resulting white precipitate was collected by filtration, washed with water and hexanes, and dried under high vacuum. This crude product was further purified using preparative reverse-phase HPLC to give {4-[1-(3-chloro-phenylmethanesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (9 mg, 18%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.44 (br. s, 1H), 7.95-8.12 (m, 1H), 7.90 (dd, J=9.03, 6.53 Hz, 1H), 7.65-7.74 (m, 2H), 7.55 (s, 1H), 7.46 (d, J=1.00 Hz, 2H), 7.36 (t, J=9.00 Hz, 1H), 4.54 (br. s., 2H), 4.13 (dd, J=5.52, 3.51 Hz, 1H), 3.78 (br. s., 4H), 3.48-3.65 (m, 1H), 2.91-3.22 (m, 3H), 2.42 (br. s., 5H), 1.69 (m, 2H). MS cald. for C25H26ClFNO4S [(M+H)+]: 490, obsd. 490.2.

Provenance & Evidence