Recycling the versatile Pipecolic linker

J Comb Chem. 2010 Sep 13;12(5):747-53. doi: 10.1021/cc100099z.

Abstract

The Pipecolic linker is a new highly versatile handle which immobilizes on solid support through a carboxylic acid function a wide range of amines, alcohols, and hydrazines. The anchoring step on pipecolic resin is very easy and efficient, and compounds are released with high purities upon acidic treatment. During this treatment, an oxazolonium intermediate is hydrolyzed, yielding the cleavage of ester or amide bond and the release of free carboxylic acid of the starting linker. In this study, we report the possibility of recycling the pipecolic resin after the use of several trifluoroacetic acid (TFA) cleavage cocktails. We demonstrate that it can be reused up to five times without significant loading decrease.

MeSH terms

  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Molecular Structure
  • Pipecolic Acids / chemical synthesis*
  • Pipecolic Acids / chemistry
  • Stereoisomerism
  • Trifluoroacetic Acid / chemistry

Substances

  • Pipecolic Acids
  • Trifluoroacetic Acid