Hydrochloric Acid → HCID 71604174, compound

Participants

Reaction Steps

To a solution [6-fluoro-3-methyl-4-(1-phenylmethanesulfonyl-piperidin-4-yl)-naphthalen-2-yl]-acetic acid methyl ester (82 mg, 0.175 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (83.8 mg, 2 mmol) in water (2 mL). The reaction mixture was stirred at room temperature overnight under nitrogen. After this time, the reaction mixture was diluted with water (˜20 mL) and then acidified with 1.0 N aqueous HCl (3.5 mL). The resulting white precipitate was collected by vacuum filtration, washed with hexanes, and then further dried under vacuum to provide [6-fluoro-3-methyl-4-(1-phenylmethane-sulfonyl-piperidin-4-yl)-naphthalen-2-yl]-acetic acid (50 mg, 63%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (br. s., 1H), 7.90 (dd, J=9.03, 6.53 Hz, 1H), 7.80-8.13 (m, 1H), 7.69 (s, 1H), 7.31-7.53 (m, 6H), 4.49 (br. s., 2H), 3.66-3.85 (m, 4H), 3.46-3.57 (m, 1H), 2.87-3.20 (m, 2H), 2.41 (br. s., 3H), 2.13-2.37 (m, 2H), 1.61-1.71 (m, 2H). MS cald. for C25H27FNO4S [(M+H)+]: 456, obsd. 456.2.

Provenance & Evidence