Sodium Hydroxide → 2-(4-Fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)1-(thiazol-2-yl)ethoxy]benzoic acid

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A mixture of methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate (2.07 g, 4.4 mmol) and sodium hydroxide (0.89 g, 22.23 mmol) in methanol (100 ml) and water (9 ml) was stirred under a nitrogen atmosphere at reflux for 18 hours, cooled to ambient temperature and the methanol evaporated off. The residue was treated with aqueous citric acid (1M, 40 ml) and extracted with dichloromethane. The organic extracts were dried and evaporated to dryness to give 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoic acid as a white foam, (1.48 g, 75%).

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