Hydrochloric Acid → 3-{[(4-{[Cyclohexyl(3,5-dimethyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl]amino}propanoic acid

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Reaction Conditions

Reaction Steps

A mixture of 2-[chloro(cyclohexyl)methyl]-3,5-dimethyl-1-benzofuran (400 mg) synthesized above, ethyl 3-{[(4-aminophenyl)carbonyl]amino}propanoate (343 mg) synthesized in Example 1(2), sodium iodide (327 mg), sodium carbonate (231 mg) and N,N-dimethylformamide (10 mL) was stirred at 80° C. for 5 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (45% ethyl acetate/hexane) to give a yellow oil. To a mixture of the obtained oil, tetrahydrofuran (5 mL) and ethanol (5 mL) 1N aqueous sodium hydroxide solution (2.00 mL) were added, and the mixture was stirred at room temperature for 2 hr, and concentrated under reduced pressure. The residue was dissolved in water (10 mL), and 1N hydrochloric acid (2.00 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (436 mg, 67%) as a white solid.

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