Hydrochloric Acid → [4-(4-Ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid

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Reaction Steps

To a solution of [4-(4-ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (36 mg, 0.08 mmol) in tetrahydrofuran (4 mL), was added 5N lithium hydroxide (6 mL). After being stirred at room temperature overnight, the resulting mixture was acidified to pH 3 with 5N hydrochloric acid, and extracted with ethyl acetate (10 mL×2). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC (gradient elution with 30-50% 0.1% trifluoroacetic acid in water in acetonitrile, 8 minutes) to give [4-(4-ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid (16 mg, 46%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.95 (dd, J=8.97, 5.68 Hz, 1H), 7.87 (s, 1H), 7.26-7.38 (m, 2H), 3.95-4.16 (m, 2H), 3.90 (s, 2H), 3.48-3.55 (m, 2H), 3.20 (br. s, 6H), 2.41 (s, 3H), 1.34 (t, J,=,7.45 Hz, 3H); MS cald. for C20H23FN2O5S 422, obsd. (ESI+) [(M+H)+] 423.

Provenance & Evidence