Methanol → 2-[(Benzo[b]thiophene-3-carbonyl)-amino]-indane-2-carboxylic acid

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Reaction Steps

A 50 mL flask containing the 2-[(benzo[b]thiophene-3-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (182, 0.40 g, 1.10 mmol) is charged with 1,4-dioxane (10 mL) and MeOH 10 mL). A stirring bar is added and stirring is initiated. After dissolution, water (5.0 mL) is added followed by the LiOH (115 mg, 2.74 mmol). After 18 h, tlc analysis (silica, 50% EtOAc/heptanes) indicates that the starting material is completely consumed. Dilute aqueous HCl (3%, ˜15 mL) and EtOAc (25 mL) are added to the reaction flask. After stirring for 10 min, the contents of the flask are poured into a reparatory funnel. The layers are separated. The aqueous layer is extracted with EtOAc (30 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 450 mg of a dry white powder.

Provenance & Evidence