Lithium hydroxide, monohydrate → HCID 71603267, compound

Participants

Reaction Steps

To a solution of {4-[1-(2,6-difluoro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (95.4 mg, 0.203 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (97.2 mg, 2.3 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred overnight at room temperature under a nitrogen atmosphere. Then, the solvent was removed and the residue was combined with water (25 mL). The mixture was neutralized with 1.0 N HCl. The resulting white precipitate was collected by filtration and dried under high vacuum to provide {4-[1-(2,6-difluoro-phenyl-carbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (59.2 mg, 64%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.46 (br. s, 1H), 8.38 (br. s, 1H), 7.90 (dd, J=9.00, 6.40 Hz, 1H), 7.75-7.85 (m, 1H), 7.65-7.74 (m, 1H), 7.24-7.42 (m, 2H), 7.14 (m, 2H), 4.17-4.38 (m, 2H), 3.79 (m, 3H), 2.99-3.24 (m, 2H), 2.44 (s, 3H), 2.13-2.36 (m, 1H), 1.57-1.73 (m, 2H). MS cald. for C25H24F3N2O3 [(M+H)+]: 457, obsd. 457.2.

Provenance & Evidence