Hydrochloric Acid → HCID 19603672, compound

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Reaction Steps

A mixture of ethyl 3-{1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-3-cyanoindol-5-yl}-2-ethoxycarbonylpropionate (0.72 g) and 1N sodium hydroxide solution (5 ml) in methanol (10 ml) was stirred under reflux for 3 hours. After cooling, the mixture was made acidic with diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in xylene (10 ml) containing acetic acid (7.5 ml) and the mixture was stirred under reflux for 7 hours. After removal of solvent by evaporation, the residue was partitioned between diluted hydrochloric acid and ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatogaphy on silica gel and eluted with a mixture of chloroform and methanol. The fractions containing the objective compounds were combined and concentrated under reduced pressure to give 3-{1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-3-cyanoindol-5-yl}propionic acid (0.78 g).

Provenance & Evidence