Full Paper

A Novel Purification Method in Organic Synthesis Using Hydrogen Bonding

  1. Bas W. T. Gruijters1,
  2. Jorge M. M. Verkade1,
  3. Floris L. van Delft1,
  4. Rint P. Sijbesma2,
  5. Pedro H. H. Hermkens3,
  6. Floris P. J. T. Rutjes1

Article first published online: 8 JUN 2007

DOI: 10.1002/ejoc.200700242

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2007, Issue 25, pages 4197–4204, September 2007

Additional Information

How to Cite

Gruijters, B. W. T., Verkade, J. M. M., van Delft, F. L., Sijbesma, R. P., Hermkens, P. H. H. and Rutjes, F. P. J. T. (2007), A Novel Purification Method in Organic Synthesis Using Hydrogen Bonding. Eur. J. Org. Chem., 2007: 4197–4204. doi: 10.1002/ejoc.200700242

Author Information

  1. 1

    Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: +31-24-365-3202

  2. 2

    Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands

  3. 3

    Organon N. V., P. O. Box 20, 5340 BH Oss, The Netherlands

Publication History

  1. Issue published online: 10 AUG 2007
  2. Article first published online: 8 JUN 2007
  3. Manuscript Received: 16 MAR 2007

Funded by

  • Netherlands Research Council for Chemical Sciences (CW)
  • Netherlands Technology Foundation (STW)

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Keywords:

  • Affinity separation;
  • Hydrogen bonding;
  • Ureidopyrimidinone;
  • Parallel synthesis;
  • Non-covalent linking

Abstract

A new workup and purification method based on quadruple hydrogen-bonding interactions is reported. Substrates containing a hydrogen-bonding affinity tag – either directly connected or through a cleavable linker – were conveniently separated from a reaction mixture and purified using a resin containing self-complementary affinity tags. Several Ugi products and nucleophilic aromatic substitution products were successfully purified by this hydrogen-bonding-based affinity-separation protocol.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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