http://dx.doi.org/10.4322/sc.2014.023

 

Synthesis of stationary phases containing pyridine, phenol, aniline and morpholine via click chemistry and their characterization and evaluation in supercritical fluid chromatography

Dunkle, Melissa; West, Caroline; Pereira, Alberto; Van der Plas, Steven; Madder, Annemieke; Farrell, William; Lesellier, Eric; Lynen, Frederic; Sandra, Pat

Palavras-chave: Packed-column supercritical fluid chromatography, Stationary phases, Click chemistry, Linear solvation energy relationships, Pharmaceuticals.

Resumo: Stationary phases containing pyridine, phenol, aniline and morpholine groups were synthesized using copper (I)-catalyzed azide-alkyne cycloaddition click reactions. The backbone of the stationary phases was aminopropyl silica. The stationary phases were evaluated in packed-column supercritical fluid chromatography (pSFC) with acidic and basic solutes without addition of additives. The analysis of metoclopromide and its impurities by SFC-time-of-flight mass spectrometry (SFC‑TOFMS) on the phenol phase is presented. In the click reaction, the 1,2,3-triazole ring is formed and to assess its influence on the polarity/selectivity, the click phases were compared to a commercial available 1,2,4-triazole hydrophilic interaction liquid chromatography (HILIC) phase. The phases were also compared to two extensively used stationary phases in SFC namely 2-ethyl pyridine and bare silica. To allow comparison with other phases used in SFC, linear solvation energy relationships (LSER) of the click phases were determined.


Referências Bibliográficas

1. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 40 (2001) 2004.
2. C. D. Hein, X.-M. Liu, D. Wang, Pharm. Res. 25, (2008) 2216.
3. H. C. Kolb, K. B. Sharpless, Drug Discov. Today 8 (2003) 1128.
4. M. Colombo, I. Peretto, Drug Discov. Today 13 (2008) 677.
5. K.M. Kacprzak, N.M. Maier, W. Lindner, Tetrahedron Lett. 47 (2006) 8721.
6. M. Slater, M. Snauko, F. Svec, J.M.J. Frechet, Anal. Chem. 78 (2006) 4969.
7. V.D. Bock, H. Hiemstra, J.H. van Maarseveen, Eur. J. Org. Chem.1 (2006) 51.
8. R. Huisgen, G. Szeimies, L. Mobius, Chem. Ber. 100 (1967) 2494.
9. F. Himo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, L. Noodleman, K.B. Sharpless, V.V. Fokin, J. Am. Chem. Soc. 127 (2004) 210.
10. Z. Guo, A. Lei, X. Liang, Q. Xu, Chem. Commun. 43 (2006) 4512.
11. Z. Guo, A. Lei, Y. Zhang, Q. Xu, X. Xue, F. Zhang, X. Liang, Chem. Commun. 24 (2007) 2491.
12. G. Lei, X. Xiong, Y. Wei, X. Zheng, J. Zheng, J. Chromatogr. A 1187 (2008) 197.
13. Y. Zhang, Z. Guo, J. Ye, Q. Xu, X. Liang, A. Lei, J. Chromatogr. A 1191 (2008) 188.
14. S. E. Van der Plas, E. Van Hoeck, F. Lynen, P. Sandra, A. Madder, Eur. J. Org. Chem. 11 (2009) 1796.
15. E. Klesper, A.H. Corwin, D.A. Turner, J. Org. Chem. 27 (1962) 700.
16. T. Berger, C. Berger, R. Majors, LCGC North America, May 1, 2010.
17. C. West, E. Lesellier, J. Chromatogr. A 1191 (2008) 21.
18. C. West, E. Lesellier, J. Chromatogr. A 1203 (2008) 105.
19. C. West, E. Lesellier, in: E. Grushka, N. Grinberg (Eds.), Advances in Chromatography, Vol. 48, CRC Press, Boca Raton, FL, 2010, pp.195
20. P. Sandra, A. Pereira, M. Dunkle, C. Brunelli, F. David, LC.GC Europe, Volume 23 (2010) 396.
21. A. Pereira, F. David, G. Vanhoenacker, C. Brunelli, P. Sandra, LC.GC North America, Volume 29 (2011) 1006
22. M.F. Vitha, P.W. Carr, J. Chromatogr. A 1126 (2006) 143.
23. J. Verron, P. Malherbe, E. Prinssen, A.W. Thomas, N. Nock, R. Masciadri, Tetrahedron Lett. 48 (2007) 377.
24. J. Blake, C.H. Li, Proc. Natl. Acad. Sci. USA 78 (1981) 4055.
25. E.A. Crowell, C.S. Ough, A. Bakalinsky, Am. J. Enol. Vitic. 36 (1985) 175.
26. F.L. Lin, H.M. Hoyt, H. van Halbeek, R. G. Bergman, C. R. Bertozzi, J. Am. Chem. Soc. 127 (2005) 2686.
27. L.T. Taylor, M. Ashraf-Khorassani, LC.GC North America, 28 (2010) 810
28. T.A. Berger, J. Chromatogr. A, doi: 10.1016/j.chroma.2011.04.071.