Lithium hydroxide, monohydrate → HCID 71603337, compound

Participants

Reaction Steps

To a solution of {4-[1-(2-chloro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (10 mg, 0.021 mmol) in THF (2.0 mL) was added a solution of lithium hydroxide monohydrate (10.2 mg, 0.426 mmol) in water (0.5 mL) at room temperature. The resulting solution was stirred for 15 hours at room temperature under nitrogen atmosphere. The solvent was removed and the aqueous layer was neutralized with 1.0N HCl. The resulting white solids were collected by filtration, washed with water and hexanes, and dried in the air to give {4-[1-(2-chloro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (4.5 mg, 46%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.42 (br. s, 1H), 7.9 (dd, J=8.91, 6.65 Hz, 1H), 7.69 (s, 1H), 7.48 (d, J=8.03 Hz, 2H), 7.25-7.42 (m, 3H), 7.09-7.23 (m, 1H), 4.27 (d, J=10.79 Hz, 2H), 3.79 (br. s, 4H), 2.43 (s, 4H), 1.65 (d, J=12.05 Hz, 3H), 1.23 (s, 2H). MS cald. for C25H25ClFN2O3 [(M+H)+] 455, obsd. 455.0.

Provenance & Evidence