2,4-Dimethoxyphenyl isocyanate → 3-(4-{2-[3-(2,4-dimethoxyphenyl)-1-heptylureido]ethoxy}phenyl)-2-ethoxypropionic Acid

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Reaction Steps

A solution of the compound obtained in Example 1, Step e (57.3 mg) in methylene chloride (4 ml) was added with 2,4-dimethoxyphenyl isocyanate (54 μl, Aldrich) and stirred for 1 hour. The reaction mixture was added with a polyamine resin (100 mg, prepared by the method described in J. Am. Chem. Soc., 119, 4874–4881, 1997), further stirred for 1 hour and filtered, and the filtrate was concentrated. The resulting residue was dissolved in ethanol (2 ml), added with 1 N aqueous sodium hydroxide (0.2 ml) and stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, added with 1 N hydrochloric acid (0.2 ml) and concentrated. The resulting residue was dissolved in methylene chloride and washed with 1 N hydrochloric acid. The solution was dried and concentrated, and the resulting residue was applied on a silica gel column and eluted with hexane/acetone (2:1, containing 0.1% acetic acid) to obtain the title compound (59 mg).

Provenance & Evidence