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

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Reaction Steps

To a solution of {6-chloro-3-methyl-4-[4-(3-phenyl-ureido)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (40 mg, 0.09 mmol) in ethanol (2 mL) and THF (3 mL) was added a solution of sodium hydroxide (262 uL, 1.0 N) at room temperature. The resulting mixture was stirred for 5 hours. Then, the solvents were removed under vacuum and the residue was diluted with water (10 mL) and acidified with 1.0 N hydrochloric acid. The mixture was allowed to stand for 3 h, then the solid was filtered off and air-dried to afford {6-chloro-3-methyl-4-[4-(3-phenyl-ureido)-phenyl]-naphthalen-2-yl}-acetic acid (37 mg, 95%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.50 (s, 1 H), 8.86 (s, 1 H), 8.77 (s, 1 H), 7.94 (d, J=8.8 Hz, 1 H), 7.84 (s, 1 H), 7.64 (d, J=8.2 Hz, 2 H), 7.41-7.58 (m, 3 H), 7.30 (t, J=7.8 Hz, 2 H), 7.19 (d, J=1.2 Hz, 1 H), 7.15 (d, J=8.5 Hz, 2 H), 6.99 (t, J=7.2 Hz, 1 H), 3.85 (s, 2 H), 2.12 (s, 3 H). HRMS calcd. for C26H22ClN2O3 [(M+H)+] 445.1314, obsd. 445.1311.

Provenance & Evidence