Lithium hydroxide, monohydrate → HCID 71603338, compound

Participants

Reaction Steps

To a solution of {6-fluoro-4-[1-(2-methoxy-phenylcarbamoyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (107.6 mg, 0.232 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (111.1 mg, 2.6 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred overnight at room temperature under a nitrogen atmosphere. The solvent was evaporated. Water (˜25 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (4.6 mL). The resulting white precipitate was collected by filtration and dried under high vacuum to provide {6-fluoro-4-[1-(2-methoxy-phenylcarbamoyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid (86.4 mg, 83%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.45 (b. s, 1H), 7.90 (dd, J=9.23, 6.59 Hz, 1H), 7.78 (br. s., 1H), 7.65-7.72 (m, 2H), 7.35 (t, J=8.01 Hz, 1H), 6.99-7.06 (m, 2H), 6.86-6.95 (m, 1H), 4.23 (m, 2H), 3.82 (s, 3H), 3.78 (br. s., 2H), 3.32 (br. s., 3H), 3.09 (br. s., 2H), 2.43 (s, 3H), 1.66 (m, 2H). MS cald. for C26H28FN2O4 [(M+H)+]: 451, obsd. 451.2.

Provenance & Evidence