Lithium hydroxide, monohydrate → HCID 71604113, compound

Participants

Reaction Steps

To a solution of [6-fluoro-4-(1-methanesulfonyl-piperidin-4-yl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (51 mg, 0.13 mmol) in THF (6.0 mL) was added a solution of lithium hydroxide monohydrate (62.1 mg, 2.6 mmol) in water (1.5 mL). The resulting solution was stirred for 15 hours at room temperature. The solvent was removed under vacuum. The residue was diluted with water (˜20 mL) and neutralized with 1.0 N aqueous HCl to form a suspension. The product was extracted into ethyl acetate (2×50 mL). The combined extracts were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to give a crude solid which was triturated with dichloromethane and hexanes. The solids were collected by filtration and washed with hexanes. After air drying, [6-fluoro-4-(1-methanesulfonyl-piperidin-4-yl)-3-methyl-naphthalen-2-yl]-acetic acid (48 mg, 94%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.4 (br. s, 1H), 7.91 (dd, J=8.91, 6.65 Hz, 2H), 7.70 (s, 1H), 7.36 (t, J=8.41 Hz, 1H), 3.78 (br. s, 6H), 2.95 (s, 3H), 2.26-2.47 (m, 6H), 1.75 (d, J=12.05 Hz, 2H). MS cald. for C19H23FNO4S [(M+H)+] 380, obsd. 380.0.

Provenance & Evidence