A Practical Synthesis of the Pseudotripeptide RC-1291

The rapid process development of a scaleable synthesis of the pseudotripeptide RC-1291 for preclinical and clinical evaluation is described. By employing a nontraditional N-to-C coupling strategy, the peptide chain of RC-1291 was assembled in high yield, with minimal racemization and in an economica...

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Bibliographic Details
Published inOrganic process research & development Vol. 10; no. 2; pp. 339 - 345
Main Authors Paul, Bernhard J, Littler, Benjamin J, Jos, Frederic, Vogt, Paul F, Pines, Seemon H
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.03.2006
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Summary:The rapid process development of a scaleable synthesis of the pseudotripeptide RC-1291 for preclinical and clinical evaluation is described. By employing a nontraditional N-to-C coupling strategy, the peptide chain of RC-1291 was assembled in high yield, with minimal racemization and in an economical manner by introducing the most expensive component last. A one-pot deprotection/crystallization procedure was developed for the isolation of RC-1291 free base, which afforded the target compound in excellent yield and with a purity of >99.5% without chromatographic purification.
ISSN:1083-6160
1520-586X
DOI:10.1021/op0502506