EDC·HCl, usually known as water soluble carbodiimide, is a versatile modern coupling agent.
Synonym: 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride
White to off-white crystalline powder
Store in a cool place
- It is an easily handled solid with high solubility in water (>200gl) and organic solvents such as dichloromethane, tetrahydrofuran and dimethylformamide.
- EDC·HCl replaced N,N-Dicyclohexylcarbodiimide (DCC) in solution-phase peptide synthesis because its urea is highly soluble in aqueous solutions, and so is easily removed by an aqueous work-up.
- As well as being used for the synthesis of amides, EDC·HCl is also used as a coupling agent in the preparation of esters from carboxylic acids using dimethylaminopyridine as the catalyst.
- Combinations of EDC·HCl and potassium salts of oximes are new and unique coupling cocktails that could be used in particular for the formation of hindered peptides such as Aib-enkephaline pentapeptide.
- DC.HCl and Potassium Salts of Oxyma and Oxyma-B as Superior Coupling Cocktails for Peptide Synthesis
Y. E. Jad, S. N. Khattab, B. G. de la Torre, T. Govender, H. G. Kruger, A. El-Faham, and F. Albericio Eur. J. Org. Chem., 2015, 14, 3116–3120.
- Evaluation of alternative solvents in common amide coupling reactions: replacement of dichloromethane and N,N-dimethylformamide
D. S. MacMillan, J. Murray, H. F. Sneddon, C. Jamieson, and A. J. B. Watson Green Chem., 2013, 15, 596–600.