Methanol → 2-[(2-Chloro-6-methyl-benzoyl)-amino]-indane-2-carboxylic acid

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Reaction Steps

A 100 mL round bottom flask containing the 2-(2-chloro-6-methyl-benzoylamino)-indane-2-carboxylic acid ethyl ester (0.255 g, 0.712 mmol) is charged with MeOH (15 mL) and a stirring bar is added. Stirring is initiated. After dissolution, water (5 mL) is added and starting material begins to precipitate out. Tetrahydrofuran is added to re-solubilize the starting material. LiOH (90 mg, 2.14 mmol) is added. After 16 h, tlc analysis (silica, 5% i-PrOH/DCM) indicates that the starting material is completely consumed. The pH of the reaction mixture is carefully adjusted to pH 3 by slowly adding dilute aqueous HCl (3%, ˜20 mL). The contents of the flask are poured into an addition funnel containing DCM (30 mL). The layers are separated. The aqueous layer is extracted with DCM (20 mL). The combined organic extracts are washed with water (30 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated to yield 280 mg of material. The material is purified by column chromatography (silica, 2% to 15% CH3OH in DCM) using an ISCO Companion and a 12 g cartridge. Fraction 2 is collected and evaporated. After pumping to constant weight, 130 mg of dry white powder is obtained.

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