Optical resolution of baclofen via diastereomeric salt pair formation between 3-(p-chlorophenyl)glutaramic acid and (S)-(-)-α-phenylethylamine

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 1997, Pages 763-768

  Caira, Mino R ^a   Clauss, Rainer ^b   Nassimbeni, Luigi R ^a   Scott, Janet L ^b   Wildervanck, Alexander F ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b Fine Chemicals Corporation   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001469854     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a606037d     Document Type: Article

References (30)

1. K. Rudnick and K. Bochow, Ger. Pat. DD 234 162, 1986; Chem. Abstr. 1987, 106, 4530c.
2. P. Hudgson and D. Weightman, Brit. Med. J., 1971, 4, 15.
3. H. R. Olpe, H. Demiéville, V. Baltzer, W. L. Benzce, W. P. Koella, P. Wolf and H. L. Haas, Eur. J. Pharmacol., 1978, 52, 133.
4. C. H. Chang, D. S. C. Yang, C. Y. Chung, W. Bi-Cheng, J. Pletcher, M. Sax and C. F. Terrence, Acta Crystallogr., Sect. B, 1982, 38, 2065.
5. (a) E. W. Wuis, E. W. J. Beneken Kolmer, L. E. C. van Beijsterveld, R. C. M. Burgers, T. B. Vree and E. v d Kleyn, J. Chromatogr., 1987, 451, 419;
6. (b) C. Vaccher, P. Berthelot and M. Debaert, J. Chromatogr., 1993, 45, 95;
7. (c) A. Sano, S. Takitani and H. Nakamura, Kuromatogurafi, 1994, 15 (4), 234.
8. (a) C. Herdies and H. P. Hubmann, Tetrahedron Asymmetry, 1992, 3 (9), 1213;
9. (b) A. Shoenfelder, A. Mann and S. Le Coz, Synlett, 1993, 1, 63;
10. (c) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302.
11. R. Chênevert and M. Desjardins, Can. J. Chem., 1994, 72, 2312.
12. Chirality in Industry. A. N. Collins, G. N. Sheldrake and J. Crosby, ed., Wiley, London, 1992, p. 20.
13. M. Sobocinska, G. Kupryszewski and M. M. Zobaczewa, Rocz. Chem., 1974, 48, 461.
14. N. A. Sivov, R. A. Gracheva, V. M. Potapov, L. G. Polevoi and I. P. Neumyvakin, Otkrytiya, Izobret., Prom. Obraztsy, Tovarnye Znaki, 1981, 17, 88 [Pat. USSR 827480/7 May (1981)].
15. F. Morlacchi, V. Losacco and V. Tortorella, Gazz. Chim. Ital., 1975, 105, 349.
16. See for example: (a) R. Yoshioka, O. Ohtsuki, T. Da-Ta, K. Okamura and M. Senuma, Bull. Chem. Soc. Jpn., 1994, 67, 3012; (b) F. J. J. Leusen, H. J. Bruins Slot, J. H. Noordijk, A. D. van der Haest, H. Wynberg and A. Bruggink, Recl. Trav. Chim. Pays-Bas, 1992, 111, 111; (c) M. Czugler, I. Csöregh, A. Kálmán, F. Faigl and M. Ács, J. Mol. Struct., 1989, 196, 157.
17. See for example: (a) R. Yoshioka, O. Ohtsuki, T. Da-Ta, K. Okamura and M. Senuma, Bull. Chem. Soc. Jpn., 1994, 67, 3012; (b) F. J. J. Leusen, H. J. Bruins Slot, J. H. Noordijk, A. D. van der Haest, H. Wynberg and A. Bruggink, Recl. Trav. Chim. Pays-Bas, 1992, 111, 111; (c) M. Czugler, I. Csöregh, A. Kálmán, F. Faigl and M. Ács, J. Mol. Struct., 1989, 196, 157.
18. See for example: (a) R. Yoshioka, O. Ohtsuki, T. Da-Ta, K. Okamura and M. Senuma, Bull. Chem. Soc. Jpn., 1994, 67, 3012; (b) F. J. J. Leusen, H. J. Bruins Slot, J. H. Noordijk, A. D. van der Haest, H. Wynberg and A. Bruggink, Recl. Trav. Chim. Pays-Bas, 1992, 111, 111; (c) M. Czugler, I. Csöregh, A. Kálmán, F. Faigl and M. Ács, J. Mol. Struct., 1989, 196, 157.
19. K. Yvon, W. Jeitschko and E. J. Parthé, J. Appl. Crystallogr., 1977, 10, 73.
20. A. C. T. North, D. C. Philips and F. S. Matthews, Acta Crystallogr., Sect. A, 1968, 24, 351.
21. G. M. Sheldrick, SHELX-86, in Crystallographic computing 3, eds. G. M. Sheldrick, C. Kruger and R. Goddard, Oxford University Press, Oxford, 1985, p. 175.
22. G. M. Sheldrick, SHELX-93: A program for Crystal Structure Determination, J. Appl. Crystallogr., in preparation, 1993.
23. H. D. Flack and D. Swarzenbach, Acta Crystallogr., Sect. A, 1988, 44, 499.
24. D. Kozma, G. Pokol and M. Ács, J. Chem. Soc., Perkin Trans. 2, 1992, 435.
25. E. Fogassy, A. Lopata, F. Faigl, F. Darvas and M. Ács, Tetrahedron Lett., 1980, 21, 647.
26. R. Taylor, O. Kennard and W. Versichel, Acta Crystallogr., Sect. B, 1984, 40, 280.
27. P. Murray-Rust and T. Glusker, J. Am. Chem. Soc., 1984, 106, 1018.
28. A. Vedani and J. D. Dunitz, J. Am. Chem. Soc., 1985, 107, 7653.
29. F. Toda, Supramolecular Chemistry, 1995, 6, 159.
30. M. Ács, Acta Chim. Hung. - Models in Chemistry, 1995, 132, 409.