Methanol → 2-[(Benzo[b]thiophene-5-carbonyl)-amino]-indane-2-carboxylic acid

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Reaction Steps

A 50 mL flask containing the 2-[(benzo[b]thiophene-5-carbonyl)-amino]-indane-2-carboxylic acid ethyl ester (184, 0.45 g, 1.25 mmol) is charged with 1,4-dioxane (8 mL) and MeOH (8 mL). A stirring bar is added and stirring is initiated. After dissolution, water (4.0 mL) is added followed by the LiOH (131 mg, 3.11 mmol). After 114 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 2 by slowly adding dilute aqueous HCl (3%, ˜12 mL). The contents of the flask are poured into a separatory funnel containing EtOAc (30 mL). The layers are separated. The aqueous layer is extracted with EtOAc (20 mL). The combined organic extracts are washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. Pumping to constant weight gives 0.42 g of off-white solid.

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