Abstract
A novel HPLC method is described for separation of the three stereoisomers of octahydroindole-2-carboxylic acid (Oic), an intermediate in the synthesis of perindopril. The chiral mobile phase contained the complex of Cu(II) with the optically active selector L-phenylalaninamide (L-PheA), and an ion-pair reagent, sodium 1-octanesulfonate. The effects of the concentrations of the Cu(II)–L-PheA complex and the ion-pair reagent, mobile phase pH, ionic strength, acetonitrile content, and column temperature were studied. Satisfactory resolution was achieved for three stereoisomers, RRR-, SSS-, and SRR-Oic.
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References
Davankov VA, Navratil JD, Walton HF (1988) Ligand exchange chromatography. CRC Press, Boca Raton, FL
Davankov VA (2003) J Chromatogr A 1000:891
Kurganov A (2001) J Chromatogr A 906:51
Vincent M, Marchand B, Remond G, Jaguelin-Guinamant S, Damien G, Portevin B, Baumal JY, Volland JP, Bouchet JP, Lambert PH, Serkiz B, Luitjen W, Laubie M, Schiavi P (1992) Drug Des Discovery 9:11
Urbach H, Henning V, Teetz R, Geiger R, Becker R, Gaul H (27 Jul 1983) EP84164 A2
Vincent M, Belierda J, Marchand B, Remond G (Dec. 1989) EP308339 A1
Cendrowska I, Bankowski K, Iskra-Jopa J (2003) Acta Pol Pharm 60:141
Davankov VA (2004) Methods Mol Biol 243:207
Wang R, Jia ZP, Hu XL, Xu LT, Li YM, Chen LR (2003) J Chromatogr B 785:353
Galaverna G, Corradini R, Dallavalle F, Folesani G, Dossena A, Marchelli R (2001) J Chromatogr A 922:151
Galaverna G, Corradini R, Dossena A, Marchelli R, Dallavalle F (1996) Chirality 8:189
Duchateau A, Crombach M, Aussems M, Bongers J (1989) J Chromatogr 461:419
Armani E, Dossena A, Marchelli R, Virgili R (1988) J Chromatogr 441:275
Armani E, Barazzoni L, Dossena A, Marchelli R (1988) J Chromatogr 441:287
Natalini B, Marinozzi M, Bade K, Sardella R, Thomsen C, Pellicciari R (2004) Chirality 16:314
Hare PE, Gil-Av E (1979) Science 204:1226
Zeng S, Zhong J, Pan L, Li Y (1999) J Chromatogr B 728:151
Galaverna G, Corradini R, Dossena A, Chiavaro E, Marchellia R, Dallavalleb F, Folesanib G (1998) J Chromatogr A 829:101
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Sun, S., Jia, Y., Zeng, N. et al. Chiral Ligand-Exchange Chromatography for Separation of Three Stereoisomers of Octahydroindole-2-carboxylic Acid. Chroma 63, 331–335 (2006). https://doi.org/10.1365/s10337-006-0752-7
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DOI: https://doi.org/10.1365/s10337-006-0752-7