Abstract
The economic and effective method for preparation ofR-(−)-ibuprofen by diastereomer crystallization was developed.R-(−)-ibuprofen was resolved from racemic ibuprofen by formingR-(−)-ibuprofen-R-(+)-α-methylbenzylamine diastereomeric salt withR-(+)-α-methylbenzylamine and crystallization. The purity ofR-(−)-ibuprofen-R-(+)-α-methylbenzylamine diastereomeric salt was tested and confirmed using HPLC and1H-NMR method. The pure diastereomeric salt collected from repeated recrystallization was further fractionated by liquid-liquid extraction to the pure enantiomer without racemization. R-(−)-ibuprofen was recovered producing overall yield of 2.4% with the purity more than 99.97%.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abushoffa, A. M., Fillet, M., Servais, A. C., Hubert, P., and Crommen, J., Enhancement of selectivity and resolution in the enantioseparation of uncharged compounds using oppositelt chargeed cyclodextrin in cappilary electrophoresis.Electrophoresis, 24, 343–350 (2003).
Bonato, P. S., Del Lama, M. P., and de Carvalho, R., Enantioselective determination of ibuprofen in plasma by high-performance liquid chromatography-electrospray mass spectrometry.J. Chromatgr. B. Analyt. Technol. Biomed. Life Sci., 796, 413–420 (2003).
Canaparo, R., Muntonim, E., Zaram, G. P., Dellapepa, C., Berno, E., Costa, M., and Eandi, M., Determination of ibuprofen in Human plasma by high performance liquid chromatography: Validation and application in pharmacokinetic study.Biomed. Chromatogr., 14, 219–226 (2000).
Ducret, A., Trani, M., Pepin, P., and Rorbert, Lorti, Chiral high performance liquide chromatography resolution of ibuprofen esters.J. Pharm. Biomed. Anal., 16, 1225–1231 (1997).
Johannsen, M., Separation of enantiomers of ibuprofen on chiral stationary phases by packed column supercritical fluid chromatography.J. Chromatogr. A, 937, 135–138 (2001).
Lana, E. Jane, Romas, J., Kazlauskas, and Quick, E., A fast Spectrophotometric Method to measure the enantioselectivity of Hydrolases.J. Org. Chem., 62, 4560–4561 (1997).
Makino, K., Yano, T., Maiguma, T., Teshima, D., Sendo, T., Itoh, Y., and Oishi, R., Arapid and simultaneous determination of several alnagesic anti-inflammatory agenr by cappilary zone electrophoresis.Ther. Drud. Monit., 25, 574–580 (2003).
Stephanie, E. Sen and Keith S. aniiker, H-NMR analysis of R/S Ibuprofen by the Formation of Diastereomeric Pair.J. Chem. Edu., 73–6, 569–572 (1996).
Van Overbeke, A., Baeyens, W., Van den Bossche, W., and Dewaele, C., Enantiomeric separation of amide derivatives of some 2-arylpropionic acids by HPLC on a cellulose-based chiral stationary phase.J. Pharm. Biomed. Anal., 12, 911–916 (1994).
Wei, W., Yu, X., u. H., Simultaneous determination of several antalgic drugs based on their interactions with betacyclodextrin by cappilary zone electrophoresis.J. Chromatogr. Sci., 42, 155–160 (2004).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Trung, T.Q., Kim, J.M. & Kim, K.H. Preparative method ofR-(−)-ibuprofen by diastereomer crystallization. Arch Pharm Res 29, 108–111 (2006). https://doi.org/10.1007/BF02977477
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02977477