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

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Reaction Steps

A solution of [3-(2-benzenesulfonyl-4-chlorobenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.16 g) in tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.5 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, pH adjusted to 4 by the addition of 0.1 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 49:1 by volume) to afford the title compound as a white solid (0.15 g).

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