An expedient method for resolution of 3-amino-3-(3′-pyridyl)propionic acid and related compounds

Organic Process Research and Development

Volumn 5, Issue 1, 2001, Pages 23-27

  Boesch, Heinz ^a   Cesco Cancian, Sergio ^b   Hecker, Leonard R ^b   Hoekstra, William J ^b   Justus, Michael ^a   Maryanoff, Cynthia A ^b   Scott, Lorraine ^b   Shah, Rekha D ^b   Solms, Guenter ^a   Sorgi, Kirk L ^b   Stefanick, Stephen M ^b   Thurnheer, Urs ^a   Villani Jr , Frank J ^b   Walker, Donald G ^b  

^a Cilag AG   (Switzerland)

^b R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035586875     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op990192m     Document Type: Article

References (26)

1. Hoekstra, W. J.; Maryanoff, B. E.; Damiano, B. P.; Andrade-Gordon, P.; Cohen, J. H.; Costanzo, M. J.; Haertlein, B. J.; Hecker, L. R.; Hulshizer, B. L.; Kauffman, J. A.; Keane, P.; McComsey, D. F.; Mitchell, J. A.; Scott, L.; Shah, R. D.; Yabut, S. C. J. Med. Chem. 1999, 42(25), 5254.
2. Hoekstra, W. J.; Maryanoff, B. E.; Andrade-Gordon, P.; Cohen, J. H.; Costanzo, M. J.; Damiano, B. P.; Haertlein, B. J.; Harris, B. D.; Kauffman, J. A.; Keane, P. M.; McComsey, D. F.; Villani, F. J., Jr.; Yabut, S. C. Bioorg. Med. Chem. Lett. 1996, 6(20), 2371.
3. Hoekstra, W. J., Ed. The Chemistry and Biology of β-Amino Acids. Curr. Med. Chem. 1999, 6(10), 905-1004.
4. Soloshonok, V. A.; Fokira, N. A.; Rybakova, A. V.; Shishkina, I. P.; Galushko, S. V.; Sorochinsky, A. E.; Kukhar, V. P.; Savchenko, M. V.; Svedas, V. K. Tetrahedron: Asymmetry 1995, 6, 1601.
5. Rico, J. G.; Lindmark, R. J.; Rogers, T. E.; Bovy, P. R. J. Org. Chem. 1993, 58, 7948.
6. (6) Behling, J. R.; Boys, M. L.; Cain-Janicki, K. J.; Colson, P.-J.; Doubleday: W. W.; Duran, J. E.; Farid, P. N.; Knable, C. M.; Muellner, F. W.; Nugent, S. T.; Topgi, R. S. PCT Int. Appl. WO 98/02410, Jan 22, 1998; Chem. Abstr. 1998, 128, 154379).
7. (6) Behling, J. R.; Boys, M. L.; Cain-Janicki, K. J.; Colson, P.-J.; Doubleday: W. W.; Duran, J. E.; Farid, P. N.; Knable, C. M.; Muellner, F. W.; Nugent, S. T.; Topgi, R. S. PCT Int. Appl. WO 98/02410, Jan 22, 1998; Chem. Abstr. 1998, 128, 154379).
8. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222.
9. Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
10. Chung, X. X. Tetrahedron: Asymmetry 1997, 8, 5.
11. Johnson, T. B.; Livak, J. E. J. Am. Chem. Soc. 1936, 58, 299 and refs 3-5 therein.
12. Castle, R. N.; Burger. A. J. Am. Pharm. Assoc. 1954, 43, 163; procedure 1 and ref 12 therein.
13. Profft, V. E.; Becker, F.-J. J. Prakt. Chem. 1965, 30(1-2), 18.
14. Secor, H. V.; Edwards, W. B., III. J. Org. Chem. 1979, 44, 3136.
15. Shih, Y.-E.; Wang, J.-S.; Chen, M.-L.: Liu, L.-K. Bull. Inst. Chem., Acad. Sin. 1989, 36, 35.
16. Zablocki, J. A.; Tjoeng, F. S.; Bovy, P. R.; Miyano, M.; Garland, R. B.; Williams, K.; Schretzman, L.; Zupec, M. E.; Rico, J. G.; Lindmark, R. J.; Toth, M. V.; McMackins, D. E.; Adams, S. P.; Panzer-Knodle, S. G.; Nicholson, N. S.; Taite, B. B.; Salyers, A. K.; King, L. W.; Campion, J. G.; Feigen, L. P. Bioorg. Med. Chem. Lett. 1995, 3(5), 539. Since no preparation of 15 was given, adaptation of methods for preparation of the isomeric N-BOC-3Pal were applied (see refs 16-19).
17. Rivier, J. E.; Porter, J.; Rivier, C. L.; Perrin, M.; Corrigan, A.; Hook, W. A.; Sigiganian, R. P.; Vale, W. W. J. Med. Chem. 1986, 29, 1846 (preparation of N-BOC derivative of D-3Pal).
18. Spencer, J. R.; Antonenko. V. V.; Delaet, N. G. J.; Goodman, M. Int. J. Pept. Protein Res. 1992, 40, 282.
19. Zablocki, J. A.; Rico, J. G.; Garland, R. B.; Rogers, T. E.; Williams, K.; Schretzman, L. A.; Rao, S. A.; Bovy, P. R.; Tjoeng, F. S.; Lindmark, R. J.; Toth, M. V.; Zupec, M. E.; McMackins, D. E.; Adams, S. P.; Miyano, M.; Markos, C. S.; Milton, M. N.; Paulson, S.; Herin, M.; Jacqmin, P.; Nicholson, N. S.; Panzer-Knodle, S. G.; Haas, N. F.; Page, J. D.; Szalony, J. A.; Taite, B. B.; Salyers, A. K.; King, L. W.; Campion, J. G.; Feigen, L. P. J. Med. Chem. 1995, 38, 2378.
20. Khalil, E. M.; Subasinghe, N. L.; Johnson, R. L. Tetrahedron Lett. 1996, 37(20), 3441.
21. The authors gratefully acknowledge helpful discussions with Drs. M. Sreenivasan and P. Knutson of SyntheTech, Albany, OR, regarding this chemistry.
22. In this instance, precipitation of the desired (S)-salt 16 was achieved using (1R,2S)-(-)-ephedrine, in contrast to the use of (1R,2S)-(+)-ephedrine for the selective precipitation of a salt of an (S)-3-vinyl containing β-amino acid; see ref 18.
23. Kersten, B. S. J. Liq. Chromatogr. 1994, 17, 33.
24. Due to a salt exchange during analysis, the HPLC chromatogram showed only the amount of each β-amino acid enantiomer present in the sample.
25. 1.2
26. Zhong, H. M.; Cohen, J. H.; Abdel-Magid, A. F.; Kenney, B. D.; Maryanoff, C. A.; Shah, R. D.; Villani, F. A., Jr.; Zhang, F.; Zhang, X. Tetrahedron Lett. 1999, 40, 7721.