1. Sequential One-Pot Synthesis of Dipeptides through the Transient Formation of CDI- N-Protected α-Aminoesters.
- Author
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de Figueiredo, Renata Marcia, Suppo, Jean ‐ Simon, Midrier, Camille, and Campagne, Jean ‐ Marc
- Subjects
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CHEMICAL synthesis , *DIPEPTIDES , *COUPLING reactions (Chemistry) , *AMINO acids , *EPIMERIZATION , *CHEMICAL reactions - Abstract
The synthesis of dipeptides through a sequential one-pot procedure from commercially available protected amino acids is described. The transformation relies on the use of in situ generated transiently CDI-protected α-amino esters (CDI, e.g. N, N′-carbonyldiimidazole). In addition of being a highly atom-economical process, the couplings take place under very mild and neutral conditions without adding a base to the reaction medium. This protocol provides a concise and less costly route to dipeptide derivatives (12 examples, up to 87% yield) and is compatible with commonly used N-urethane protecting groups. Moreover, no epimerization was detected even when sensitive Boc-Cys(Bn)−OH was used. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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