Lithium hydroxide, monohydrate → HCID 71603268, compound

Participants

Reaction Steps

To a solution of {4-[1-(2,4-dichloro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (74.8 mg, 0.149 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (71.4 mg, 1.7 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 (˜20 mL) was added and the mixture was neutralized with 1.0 N HCl (30 mL). The resulting white precipitate was collected by filtration and dried under high vacuum overnight to provide {4-[1-(2,4-dichloro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (57.8 mg, 80%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.5 (br. s, 1H), 8.46 (br. s, 1H), 7.90 (dd, J=8.80, 6.50 Hz, 1H), 7.76-7.86 (m, 1H), 7.68 (m, 2H), 7.50 (d, J=8.78 Hz, 1H), 7.40 (dd, J=8.70, 2.30 Hz, 1H), 7.30-7.37 (m, 1H), 4.20-4.32 (m, 2H), 3.68-3.97 (m, 4H), 3.02-3.24 (m, 2H), 2.43 (s, 3H), 2.16-2.40 (m, 2H), 1.61-1.70 (m, 2H). MS cald. for C25H24Cl2FN2O3 [(M+H)+]: 489, obsd. 489.1.

Provenance & Evidence