Sodium Hydroxide → {6-Chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid

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Reaction Steps

To a solution of {6-chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (85 mg, 0.17 mmol) in ethanol (7 mL) was added a solution of sodium hydroxide solution (516 uL, 1.0 N) at room temperature. The resulting clear solution was stirred overnight. Then, the solvents were removed under vacuum and the residue was diluted with water (10 mL), acidified with 1.0 N hydrochloric acid, and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (20 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum provided the desired {6-chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid as a light brown foam. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.44 (br. s, 1 H), 10.54 (br. s, 1 H), 7.88-7.95 (m, 2 H), 7.82 (s, 1 H), 7.48-7.58 (m, 1 H), 7.35-7.46 (m, 3 H), 7.22 (d, J=8.5 Hz, 2 H), 7.08 (d, J=8.5 Hz, 2 H), 6.92 (d, J=1.5 Hz, 1 H), 3.80 (s, 2 H), 2.63 (s, 3 H), 1.99 (s, 3 H). HRMS calcd. for C26H21ClNO4S [(M−H)−] 478.0885, obsd. 478.0885.

Provenance & Evidence