Lithium hydroxide, monohydrate → HCID 71603263, compound

Participants

Reaction Steps

To a colorless solution of {4-[1-(2,4-dichloro-benzoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (102 mg, 0.21 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (100 mg, 4.2 mmol) in water (2.0 mL) at room temperature. The resulting colorless solution was stirred for 15 hours. The solvent was removed and the aqueous solution after dilution with water was neutralized with 1.0 N aqueous HCl. The resulting white precipitate was collected by filtration and washed with hexanes. After drying in the air, 62 mg of the crude product was isolated as a white solid. The crude product was dissolved in ethyl acetate (˜3 mL) with heating and the resulting solution was diluted with hexanes (˜20 mL). The solution was stored in the freezer for three days and the precipitated solids were collected by filtration and washed with hexanes. After drying in air, {4-[1-(2,4-dichloro-benzoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (48 mg, 48%) was isolated as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.42 (br. s, 1H), 7.85-7.97 (m, 1H), 7.81 (br. s, 1H), 7.75 (s, 1H), 7.69 (s, 1H), 7.51-7.63 (m, 1H), 7.41-7.50 (m, 1H), 7.35 (t, J=8.03 Hz, 1H), 4.71 (br. s, 1H), 3.78 (br. s, 4H), 3.40 (br. s, 2H), 2.42 (br. s, 3H), 1.77 (br. s, 2H), 1.60 (d, J=9.79 Hz, 2H). MS cald. for C25H23Cl2FNO3 [(M+H)+] 474, obsd. 474.1.

Provenance & Evidence