Water → HCID 59314339, compound

Participants

Reaction Steps

A 40 mL vial containing the 2-(3-methoxy-2-methyl-benzoylamino)-indane-2-carboxylic acid ethyl ester (0.65 g, 1.84 mmol) is charged with THF (10 mL) MeOH (10 mL) and a stirring bar is added. Stirring is initiated. After dissolution, water (5 mL) is added followed by the LiOH (267 mg, 6.36 mmol). After 36 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%, ˜10 mL). The contents of the flask are poured into an addition 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 to yield 620 mg of amorphous white solid. The sample is purified by column chromatography (silica, 2% to 15% CH3OH in DCM) using an ISCO Companion and a 40 g cartridge. Fractions 14-16 are collected and evaporated by pumping to constant weight gives 380 mg of dry white powder.

Provenance & Evidence