Imidazole-1-sulfonyl azide-based diazo-transfer reaction for the preparation of azido solid supports for solid-phase synthesis

ACS Comb Sci. 2013 Jul 8;15(7):331-4. doi: 10.1021/co4000437. Epub 2013 Jun 6.

Abstract

An efficient, standard, mild, and copper-free imidazole-1-sulfonyl azide hydrochloride-based diazo-transfer method was implemented in a set of four resins that cover a broad range of hydrophobicity. The imidazole-1-sulfonyl azide hydrochloride is easily prepared/commercially available, stable upon storage at 4 °C, and proved to be a suitable alternative to triflyl azide for diazo-transfer reactions in amine functionalized resins. We have successfully applied the azido resins for the conjugation of a TFA-labile Wang-type linker using Click Chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Azides / chemistry*
  • Click Chemistry
  • Imidazoles / chemistry*
  • Solid-Phase Synthesis Techniques
  • Sulfones / chemistry*

Substances

  • Amines
  • Azides
  • Imidazoles
  • Sulfones
  • imidazole-1-sulfonyl azide
  • imidazole-1-sulfonyl azide hydrochloride