Synthesis of N-methylpyrrole and N-methylimidazole amino acids suitable for solid-phase synthesis

J Org Chem. 2004 Nov 12;69(23):8151-3. doi: 10.1021/jo048686r.

Abstract

New and higher yielding synthetic routes to N-protected N-methylpyrrole and N-methylimidazole amino acids are introduced to circumvent difficulties associated with established schemes. Key steps in each synthesis include copper-mediated cross-coupling reaction to directly install a carbamate-protected 4-amine in the N-methylpyrrole derivative and effective nitration followed by a one-pot reduction/Boc protection of the amine in the synthesis of the N-Me-imidazole amino acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Combinatorial Chemistry Techniques
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry

Substances

  • Amino Acids
  • Imidazoles
  • Pyrroles