Methanol → 2-[(2,2-Dimethyl-2,3-dihydro-benzofuran-7-carbonyl)-amino]-indan-2-carboxylic acid

Participants

Reaction Steps

A 50 mL round bottom flask containing the 2-[(2,2-dimethyl-2,3-dihydro-benzofuran-7-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (0.45 g, 1.179 mmol) is charged with MeOH (25 mL) and a stirring bar is added. Stirring is initiated. After dissolution, water (8 mL) and the LiOH (108 mg, 2.58 mmol) are added. After 56 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 a reparatory 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 (30 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. Pumping to constant weight gives 460 mg of material. The sample is purified by column chromatography (silica, 2% to 15% CH3OH in DCM) using an ISCO Companion and a 12 g cartridge. Fraction 3 is collected and evaporated. After pumping to constant weight, 375 mg (90%) of a dry white powder is obtained.

Provenance & Evidence