Lithium hydroxide, monohydrate → HCID 71603265, compound

Participants

Reaction Steps

To a solution of {4-[1-(2,5-difluoro-benzoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (73 mg, 0.160 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (76.6 mg, 1.8 mmol) in water (2 mL). The reaction mixture was stirred at room temperature overnight. After this time, the reaction mixture was concentrated. Water (˜20 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (3.2 mL). The resulting white precipitate was collected by vacuum filtration, washed with hexanes, and then further dried under vacuum to give {4-[1-(2,5-difluoro-benzoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (57.5 mg, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.46 (br. s, 1H), 7.80-8.20 (m, 1H), 7.90 (dd, J=9.00, 6.50 Hz, 1H), 7.69 (s, 1H), 7.31-7.52 (m, 4H), 4.62-4.77 (m, 1H), 3.68-4.08 (m, 4H), 3.48-3.60 (m, 1H), 2.95-3.21 (m, 1H), 2.43 (br. s., 3H), 2.11-2.34 (m, 2H), 1.57-1.82 (m, 2H). MS cald. for C25H23F3NO3 [(M+H)+]: 442, obsd. 442.2.

Provenance & Evidence