Resolution of ibuprofen with primary amine carbamates in supercritical carbon dioxide

Authors

  • László Lőrincz
    Affiliation
    Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1111 Budapest, Budafoki út 6–8., Hungary
  • Zsolt Hovonyecz
    Affiliation
    Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1111 Budapest, Budafoki út 6–8., Hungary
  • János Madarász
    Affiliation
    Department of Inorganic and Analytical Chemistry, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1111 Budapest, Szent-Gellért tér 4., Hungary
  • Erzsébet Varga
    Affiliation
    Cyclolab Ltd., H-1111 Budapest, Illatos út 7., Hungary
  • Edit Székely
    Affiliation
    Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1111 Budapest, Budafoki út 6–8., Hungary
https://doi.org/10.3311/PPch.12918

Abstract

Three new, successful resolving agents, namely (S)-2-phenylglycinol, (R)-1-phenylethanaminium (R)-(1-phenylethyl) carbamate and (S)-2-hydroxy-1-phenylethanaminium (S)-(2-hydroxy-1-phenylethyl) carbamate of ibuprofen are presented. The carbamate salts are stable white crystals, they can be easily stored and handled. All salt forming resolution were performed in supercritical carbon dioxide as the only solvent. The enantioseparations were efficient (approx. 50 % enantiomeric purities, > 90 % yields in the crystalline phase) and robust. Unlike previous experiences with primary amine resolving agents, the diastereomeric salt formations and resolutions were competed in short times, even within one hour suggesting that the carbamates are intermediates of the salt formation reaction.

Keywords:

supercritical carbon dioxide, chiral, salt formation, optical resolution, carbamate, activation

Citation data from Crossref and Scopus

Published Online

2019-03-18

How to Cite

Lőrincz, L., Hovonyecz, Z., Madarász, J., Varga, E., Székely, E. “Resolution of ibuprofen with primary amine carbamates in supercritical carbon dioxide”, Periodica Polytechnica Chemical Engineering, 63(2), pp. 312–317, 2019. https://doi.org/10.3311/PPch.12918

Issue

Section

Articles