Synthesis of isotopomers of N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester: Choice of cyanation solvent

Christopher G. Bazewicz, Jacob S. Lipkin, Kristen A. Lozinak, Matthew D. Watson, Scott H. Brewer

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

N-(tert-butoxycarbonyl)-4-cyano-l-phenylalanine methyl ester and three isotopomers (C15N, 13CN, and 13C15N) were successfully synthesized in two steps to expand the utility of the nitrile symmetric stretch vibration of this modified amino acid as a vibrational reporter of local environments. The choice of cyanation solvent directly impacted the level of isotopic enrichment of the isotopomers. The commonly used solvent acetonitrile resulted in an isotopic enrichment of only ∼80% with a cyanation reaction time of 4.5 h, however, the cyanation solvent N,N-dimethylformamide afforded the isotopomers with >98% isotopic enrichment.

Original languageEnglish (US)
Pages (from-to)6865-6868
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number51
DOIs
StatePublished - Dec 21 2011

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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