3-Acetamidophthalic Anhydride → alpha-Hexyl-4-{[3-(acetylamino)-2-carboxybenzoyl]-amino}-1H-imidazole-1-acetic acid ethyl ester

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Reaction Steps

Following the procedure of Example 2, 1.54 g of 4-nitro-α-hexyl-1H-imidazole-1-acetic acid ethyl ester were hydrogenated to the corresponding amine and allowed to react with 1.12 g of 3-acetamidophthalic anhydride in ethyl acetate. After stirring at room temperature, the solution was concentrated in vacuo and a small amount ethyl acetate added. After sitting overnight, the resulting solid was collected by filtration. Crystallization from hot ethyl acetate/methanol/hexanes provided 0.54 g of the desired intermediate, m.p. 144°-145° C. NMR.

Provenance & Evidence