Methanol → 4-(5-Fluoro-6-(3-fluoroazetidine-1-carbonyl)pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid

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Reaction Steps

To a solution of methyl 4-(5-fluoro-6-(3-fluoroazetidine-1-carbonyl)pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydrobenzofuran-6-carboxylate (1.520 g, 3.633 mmol), in 10 mL THF and 10 mL MeOH was added 4.25 mL of 1N aqueous NaOH. The resulting solution was stirred at room temperature for 2 hr. The solvent was removed in vacuo. Water was added, and the mixture was washed with EtOAc. The aqueous layer was acidified with 1N HCl until pH˜1, and extracted with 3×EtOAc. The combined organic layer was dried over Na2SO4 and concentrated to give a white foam (1.32 g, 90% yield), which contains ˜15% impurity. LCMS for C20H18F2N2O5 m/z 405.20 (M+H)+.

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