Lithium Hydroxide → 4-(1-(4-chloro-2-methoxyphenyl)-3-(hydroxymethyl)-1H-pyrrol-2-yl)-3-methylbenzamide

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Reaction Steps

To a solution of ethyl 3-(2-(4-carbamoyl-2-methylphenyl)-1-(4-chloro-2-methoxyphenyl)-1H-pyrrol-3-yl)propanoate (580 mg, 1.3 mmol) in MeOH (5 mL) was added aqueous LiOH solution (2 mol/L, 5 mL), and the reaction mixture was stirred at room temperature for three hours. TLC (PE: EtOAc=1:2) showed that the starting material was consumed. The aqueous layer was washed with EtOAc (10 mL), and acidified by 0.5 N HCl to pH=2. The aqueous layer was extracted with a mixture of EtOAc and MeOH (v/v=10:1, 20 mL×3), and the combined organic layer was washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography and preparative HPLC to afford the titled compound as an off-white solid (68.3 mg, yield: 12.6%).

Provenance & Evidence