Lithium hydroxide, monohydrate → HCID 71604238, compound

Participants

Reaction Steps

To a solution of [4-(1-cyclopentanesulfonyl-piperidin-4-yl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (64.8 mg, 0.145 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (69.5 mg, 1.7 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred for three hours under a nitrogen atmosphere. The solvent was evaporated. Water (20 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (3 mL). The resulting white precipitate was collected by filtration, washed with water and hexanes, and dried under high vacuum. This crude product was further purified using preparative reverse-phase HPLC to give [4-(1-cyclopentane-sulfonyl-piperidin-4-yl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid (19 mg, 30%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (br. s., 1H), 7.97-8.17 (m, 1H), 7.90 (dd, J=9.03, 6.53 Hz, 1H), 7.69 (s, 1H), 7.35 (t, J=7.53 Hz, 1H), 3.78 (br. s., 6H), 3.11 (br. s., 2H), 2.42 (br. s., 4H), 1.96-2.08 (m, 2H), 1.80-1.93 (m, 2H), 1.53-1.78 (m, 6H). MS cald. for C23H29FNO4S [(M+H)+]: 434, obsd. 434.2.

Provenance & Evidence