Lithium hydroxide, monohydrate → HCID 71604239, compound

Participants

Reaction Steps

To a solution of {6-fluoro-3-methyl-4-[1-(pyrrolidine-1-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (86.5 mg, 0.193 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (92.4 mg, 2.2 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred overnight under a nitrogen atmosphere. The solvent was evaporated. Water (20 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (4 mL). The resulting white precipitate was collected by filtration, washed with water and hexanes, and dried under high vacuum to give {6-fluoro-3-methyl-4-[1-(pyrrolidine-1-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (55.7 mg, 66%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.44 (br. s., 1H), 8.07 (br. s, 1H), 7.90 (dd, J=9.0, 6.5 Hz, 1H), 7.69 (s, 1H), 7.35 (td, J=8.5, 2.0 Hz, 1H), 3.78 (br. s., 4H), 3.22-3.43 (m, 5H), 3.09 (br. s., 2H), 2.42 (br. s., 3H), 1.81-1.97 (m, 4H), 1.67 (bd, 2H). MS cald. for C22H28FN2O4S [(M+H)+]: 434, obsd. 434.2.

Provenance & Evidence