Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents |
| |
| Authors: | Jordi Alsina George Barany Fernando Albericio Steven A. Kates |
| |
| Affiliation: | (1) Department of Chemistry, University of Minnesota, Minneapolis, MN, 55455, U.S.A;(2) Department of Organic Chemistry, University ofBarcelona, Barcelona, E-08028, Spain;(3) PerSeptive Biosystems Inc., 500 Old Connecticut Path, Framingham, MA, 01701, U.S.A. |
| |
| Abstract: | Pyrrolidide derivatives are observed as unwanted by-products from slow reactions of activated carboxylates with nucleophilic amines, as mediated by phosphonium salt coupling reagents (PyAOP, PyBOP, PyBroP). This side reaction is attributed to the presence of small amounts (e.g., 0.5%, w/w) of pyrrolidine as a contaminant to commercial phosphonium salts, and does not occur when the reagents are crystallized before their use in coupling reactions. |
| |
| Keywords: | PyAOP PyBOP PyBroP side reactions solid-phase peptide synthesis |
| 本文献已被 SpringerLink 等数据库收录！ |
|
