Sodium Hydroxide → (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid

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Reaction Steps

An aqueous 1N solution of sodium hydroxide (0.9 mL, 0.9 mmol) was added to a solution of (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester (Example 226; 140 mg, 0.272 mmol) in methanol/tetrahydrofuran (1:1; 3.6 mL). The solution was stirred at room temperature for 16 h and the solvent was evaporated. Water (7 mL) was added and the mixture was extracted with diethyl ether. The diethyl ether extract was discarded and the water layer was filtered through Celite® and then acidified with 1N hydrochloric acid solution (1 mL). The resulting solid was filtered off, washed with water, dried and crystallized from tetrahydrofuran/methanol/water to give (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid (96 mg, 70% yield) as a colorless solid.

Provenance & Evidence