An efficient access to the enantiomers of α-methyl-4-carboxyphenylglycine via a hydantoin route using a practical variant of preferential crystallization. AS3PC (auto seeded programmed polythermic preferential crystallization)

Tetrahedron Asymmetry

Volumn 8, Issue 17, 1997, Pages 2913-2920

  Ndzie E ^a   Cardinael, P ^a   Schoofs, A R ^b   Coquerel, G ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b Ctr Europ de Bioprospective   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYL 4 CARBOXYPHENYLGLYCINE; HYDANTOIN DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; REPRODUCIBILITY; TECHNIQUE;

EID: 0030822143     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00349-2     Document Type: Article

References (22)

1. (a) D. Obrecht, U. Bohdal, J. Daly, C. Lehmann, P. Schönholzer and K. Müller Tetrahedron 1995, 51, 40, 10883-10900.
2. (b) D. Obrecht, U. Bodhal, C. Broger, D. Bur, C. Lehmann, R. Ruffieux, P. Schönholzer, C. Spiegler and K. Müller ibid. 1995, 78, 563-580.
3. (a) D. Obrecht, C. Spiegler, P. Schönholzer, K. Müller, H. Heimgartner and F. Stierli Helv. Chim. Acta 1992, 75, 1666-1696.
4. (b) D. Obrecht, H. Karajiannis, C. Lehmann, P. Schönholzer, C. Spiegler and K. Müller ibid 1995, 78, 703-714.
5. M. Kemp, P. Roberts, P. Pook, D. Jane, A. Jones, P. Jones, D. Sunter, P. Udvarhelyi and J. Watkins Eur. J. Pharm. Mol. Pharm. Section 1994, 266, 187-192.
6. (a) S. R. Glaum, D. C. Sunter, P. M. Udvarhelyi, J. C. Watkins and R. J. Miller Neuropharmacology 1993, 32, 1419-1425.
7. (b) J. Watkins and G. Collingridge Trends. Pharmacol. Sci. 1994, 15, 333-342.
8. E. Coudert, F. Acher and R. Azerad Tetrahedron: Asymmetry 1996, 7, 2963-2970.
9. H. R. Henze and A. Furman Isbell J. Am. Chem. Soc. 1954, 76, 4152-4156.
10. H. R. Henze and Robert J. Speer J. Am. Chem. Soc. 1942, 64, 522-523.
11. (a) H. T. Bücherer and V. A. Lieb J. Prakt. Chem. 1934, 141, 5
12. (b) L. H. Goodson, I. L. Honigberg, J. J. Lehman and W. H. Burton J. Org. Chem. 1960, 25, 1920-1924.
13. J. Jacques, A. Collet and S. H. Wilen Enantiomers, Racemates and Resolutions, Krieger Publishing Company, Malabar Florida, 1994.
14. E. Eliel, S. H. Wilen and L. N. Mander Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994, 153-214, 297-322.
15. G. Coquerel, M.-N. Petit and R. Bouaziz. PCT Patent WO 95/08522.
16. G. Coquerel, M.-N. Petit, R. Bouaziz and D. Depernet Chirality 1992, 4, 400-403.
17. E. Ware Chem. Rev. 1950, 46, 403-470.
18. G. Coquerel and S. Petit J. Cryst. Growth. 1993, 130, 173-180.
19. Noguchi Institute English Patent no 1 197-809.
20. M. J. Brienne, A. Collet and J. Jacques Synthesis 1983, 9, 704-705.
21. G. Amiard Bull. Soc. Chim. Fr. 1956, 447.
22. E. Ndzié, G. Coquerel Unpublished results.