Skip to main content
SpringerLink
Log in

Synthesis of chiral N-protected amino acid esters by the use of UNCAs

  • Published:
Letters in Peptide Science Aims and scope Submit manuscript

Summary

An easy synthesis of N-protected amino acid esters, including tert-butyl esters, is described by the use of urethane N-protected carboxyanhydrides (UNCAs). Treating UNCAs with tert-butanol in the presence of potassium bicarbonate at 45°C yielded the corresponding N-protected amino acid tert-butyl esters in a very simple way. Benzyloxycarbonyl and tert-butyloxycarbonyl N-protected amino acid tert-butyl esters have been obtained by this procedure. Once more, this reaction showed the great reactivity of UNCAs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Fuller, W.D., Cohen, M.P., Shabankareh, M. and Blair, R.K., J. Am. Chem. Soc., 112 (1990) 7414.

    Google Scholar 

  2. Xue, C. and Naider, F., J. Org. Chem., 58 (1993) 350.

    Google Scholar 

  3. Rodriguez, M., Califano, J.C., Loffet, A. and Martinez, J., In Schneider, C.H. and Eberle, A.N. (Eds.) Peptides 1992 (Proceedings of the 22nd European Peptide Symposium), ESCOM, Leiden, 1993, pp. 233–234.

  4. Fehrentz, J.A., Califano, J.C., Amblard, M., Loffet, A. and Martinez, J., Tetrahedron Lett., 35 (1994) 569.

    Google Scholar 

  5. Fehrentz, J.A., Bourdel, E., Califano, J.C., Chaloin, O., Devin, C., Garrouste, P., Lima-Leite, A.C., Llinares, M., Rieunier, F., Vizavonna, J., Winternitz, F., Loffet, A. and Martinez, J., Tetrahedron Lett., 35 (1994) 1557.

    Google Scholar 

  6. Fehrentz, J.A., Pothion, C., Califano, J.C., Loffet, A. and Martinez, J., Tetrahedron Lett., 35 (1994) 9031.

    Google Scholar 

  7. Fehrentz, J.A., Genu-Dellac, C., Amblard, M., Winternitz, F., Loffet, A. and Martinez, J., J. Pept. Sci., 1 (1995) 124.

    Google Scholar 

  8. Zhu, Y.-F., Blair, R.K. and Fuller, W.D., Tetrahedron Lett., 35 (1994) 4673.

    Google Scholar 

  9. Chevallet, P., Garrouste, P., Malawska, B. and Martinez, J., Tetrahedron Lett., 34 (1993) 7409.

    Google Scholar 

  10. Anderson, G.W. and Callahan, F.M., J. Am. Chem. Soc., 82 (1960) 3359.

    Google Scholar 

  11. Wunsch, E. and Zwick, A., Hoppe-Seyler's Z. Physiol. Chem., 333 (1963) 108.

    Google Scholar 

  12. Wakimasu, M., Kitada, C. and Fujino, M., Chem. Pharm. Bull., 29 (1981) 2592.

    Google Scholar 

  13. Castro, B., Evin, G., Selve, C. and Seyer, R., Synthesis, (1977) 413.

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie et Pharmacologie de Molécules d'Intérêt Biologique, URA CNRS 1845, Faculté de Pharmacie, 15 avenue C. Flahault, F-34060, Montpellier, France

    P. Chevallet, J.-A. Fehrentz, C. Devin, J. Castel & J. Martinez

  2. Propeptide, F-91710, Vert le Petit, France

    A. Loffet

  3. Zaklad Technologi Chemicznej Srodkow Leczniczych, Collegium Medicum Universytetu Jagielonskiego, Ul. Medyczna 9, 30-688, Krakow, Poland

    K. Kiec-Kononowicz

Authors
  1. P. Chevallet
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J.-A. Fehrentz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Kiec-Kononowicz
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. C. Devin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. J. Castel
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. Loffet
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. J. Martinez
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chevallet, P., Fehrentz, JA., Kiec-Kononowicz, K. et al. Synthesis of chiral N-protected amino acid esters by the use of UNCAs. Lett Pept Sci 2, 297–300 (1996). https://doi.org/10.1007/BF00142242

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00142242

Keywords

Search

Navigation