1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → L-Aspartic Acid

Participants

Reaction Conditions

Reaction Steps

To a stirred turbid mixture of N-[valinyl]aspartic acid, α-methyl, β-tert-butyl diester (2.75 g, 9.11 mmol) and 1,3-dimethylindole-2-carboxylic acid (1.95 g, 10 10.3 mmol) in DMF (30 ml) was added 4-dimethylaminopyridine (DMAP) (1.26 g, 10.3 mmol) and EDAC (2.37 g, 12.4 mmol). The reaction mixture was stirred under a nitrogen atmosphere at 0° C. for 1 hour and at room temperature for 3 hours. The reaction mixture was then partitioned between ethyl acetate and 5% KHSO4 solution and the aqueous solution was back-extracted with ethyl acetate. The combined extracts were washed with saturated NaHCO3 solution, water, and brine, dried over sodium sulfate, and concentrated to give a solid. The solid was triturated with ether to give N-[1,3-dimethyl-indole-2-carbonyl) valinyl]aspartic acid, α-methyl, β-tert butyl diester as a white powder (2.87 g, 67%).

Provenance & Evidence