Lithium Hydroxide → [3-(4-Benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid

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A mixture of [3-(4-benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.065 g), tetrahydrofuran (20 mL) and 1.0 M aqueous lithium hydroxide solution (4.0 mL) was stirred at room temperature for 5 minutes. The mixture was concentrated under reduced pressure, acidified by the addition of 1.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 19:1 by volume) to afford the title compound as a white solid (0.050 g).

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