Synthesis of N-t-boc-4-s-t-butyl-L-thiophenylalanine via palladium catalyzed cross-coupling reaction of N-t-boc-4-iodo-L-phenylalanine with t- butylthiol or sodium t-butylthiolate

Synthetic Communications

Volumn 26, Issue 7, 1996, Pages 1431-1440

  Rajagopalan, Shyamala ^a   Radke, Gary ^a   Evans, Michelle ^a   Tomich, John M ^a  

^a KANSAS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENYLALANINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030003430     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003505     Document Type: Article

References (32)

1. a. Roberts, D.C.; Vellaccio, F. Unusual α-Amino Acids in Peptide Synthesis. In "The Peptides": Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1983, Chap 6.
2. b. Williams, R.M. "Synthesis of Optically Active α - Amino Acids". Pergamon Press: Oxford. 1989.
3. c. Hruby V.J. Biopolymers, 1993, 33, 1073-1082.
4. d. Duthaler, R.O. Tetrahedron, 1994, 50, 1539-1650.
5. e. Steele, F.R. The Journal of NIH Research, 1995, 7, 43-45.
6. Pinilla, C.; Appel, J.; Blondelle, S.; Dooley, C.; Dörner, B.; Eichler, J.; Ostresh, J.; Houghten, R.A. Biopolymers (Peptide Science),1995, 37, 221-240.
7. Lung, F.-D.; Li, G.; Lou, B.-S.; Hruby, V.J.Synth. Commun. 1995, 25, 57-61.
8. Xiang, L.; Wu, H.; Hruby, V.J. Tetrahedron: Asymmetry. 1995, 6, 83-86.
9. Cativiela, C.; Diaz-de-Villegas, M.D.; Galvez, J.A. Tetrahedron. 1994, 50, 9837-9846.
10. Majer, P.; Slaninova, J.; Lebl, M. Int. J. Peptide Protein Res. 1994, 43, 62-68.
11. Stokker, G.E.; Hoffman, W.F.; Homnick, C.F. J. Org. Chem. 1993, 58, 5015-5016.
12. Franz, R.G.; Weinstock, J.; Calvo, R.R.; Samanen, J.; Aiyar, N. Organic Preparations and Procedures Int. 1994, 26, 533-538.
13. Lei, H.; Stoakes, M.S.; Herath, K.P.B.; Lee, J.; Schwabacher, A.W. J. Org. Chem. 1994, 59, 4206-4210.
14. Gordeev, M.F.; Patel, D.V.; Barker, P.L.; Gordon, E.M. Tetrahedron Lett. 1994, 35, 7585-7588.
15. a. Burley, S.K.; Petsko, G.A.; in:Weakly Polar Interactions in Proteins, in "Advances in Protein Chemistry", Anfinsen, C. B.; Edsall, J.T.; Richards, F.M.; Eisenberg, D.S. Eds., Academic Press, Inc: San Diego, CA, 1988, pp125-186.
16. b. "Peptides:Design, Synthesis and Biological Activity", Basava, C.; Anantharamaiah, G.M. Eds., Birkhauser: Boston,1994.
17. Bodanszky, M. " Principles of Peptide Synthesis". Springer-Verlag: Berlin. 1993.
18. Escher, E.; Bernier, M.; Parent, P. Helv. Chim. Acta. 1983, 66, 1355-1365.
19. We thank Prof. Escher for sending us some of the thiophenylalanine samples synthesized using the procedure in ref 13 and for sharing with us their experience in carrying out that synthesis.
20. a. Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13-14.
21. b. Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385-1389.
22. a. Tilley, J.W.; Sarabu, R.; Wagner, R.; Mulkerins, K. J. Org. Chem. 1990, 55, 906-910.
23. b. Shieh, W.-C.; Carlson, J. A. J. Org. Chem. 1992, 57, 379-381.
24. c. Burk, M.J.; Lee, J.R.; Martinez, J.P. J. Am. Chem. Soc. 1994, 116, 10847-10848.
25. Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron Lett.1995, 36, 4133-4136.
26. a. Pastuszak, J.J.; Chimiak, A. J.Org.Chem. 1981, 46, 1868-1873.
27. b. Nishimura, O.; Kitada, C.; Fujino, M. Chem. Pharm. Bull. 1978, 26, 1576-1585.
28. c. Akaji, K.; Nishiuchi, H.; Kiso, Y. Tetrahedron Lett., 1995, 36, 1875-1878 and references cited therein.
29. Personal communication with Prof. A.W. Schwabacher, Department of Chemistry, Iowa State University, Ames, Iowa 50011.
30. Hegedus, L.S. Palladiun in Organic Synthesis. In "Organometallics in Synthesis", Schlosser, M. Ed.; John Wiley & Sons: England, 1994, Chap 5.
31. R 2 = 23.8 min and 3 = 26.3 min.
32. Takagi, K.; Sasaki, K.; Sakakibara, Y. Bull. Chem. Soc. Jpn., 1991, 64, 1118-1121.