Lithium Hydroxide → HCID 71604171, compound

Participants

Reaction Steps

To a colorless solution of {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (109 mg, 0.208 mmol) in THF (8.0 mL) was added a solution of an excess lithium hydroxide (100 mg, 4.18 mmol) in water (2.0 mL) at room temperature. The resulting light yellow solution was stirred for 15 hours. The reaction mixture was concentrated and the aqueous solution was diluted with water then neutralized with 1.0 N aqueous HCl. The resulting suspension was extracted into ethyl acetate (2×40 mL). The combined extracts were washed with brine and dried over anhydrous MgSO4, filtered, and concentrated to afford {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (105 mg, 99%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.32 (br. s, 1H), 8.06 (d, J=8.5 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.88 (dd, J=8.5, 6.8 Hz, 1H), 7.64-7.82 (m, 3H), 7.25-7.39 (m, 1H), 3.82-3.94 (m, 2H), 3.76 (br. s, 2H), 3.47-3.72 (m, 1H), 3.07 (br. s, 2H), 2.36 (s, 3H), 2.09-2.46 (m, 2H), 1.68 (d, J=12.0 Hz, 2H). MS cald. for C24H23Cl2FNO4S [(M+H)+] 510, obsd. 510.1.

Provenance & Evidence