Dicyclohexylcarbodiimide → N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-hydroxy-methyl]-benzamide

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Reaction Steps

Add dicyclohexylcarbodiimide (0.231 g, 1.12 mmol, Aldrich Chemical Co.) to a solution of N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-isophthalamic acid (0.500 g, 1.12 mmol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (0.161 g, 1.12 mmol), and 4-N,N-dimethylaminopyridine (0.273 g, 2.23 mmol, Chem-Impex) in dichloromethane (50 mL, 0.2 M). Filter precipitate, wash filter cake with dichloromethane, and concentrate filtrate. Dilute residue with dichloromethane and wash with 1N hydrochloric acid. Dry the organic layer with sodium sulfate and concentrate to afford the title compound (0.641 g, 1.12 mmol): MS (m/z): 572 (M−1).

Provenance & Evidence