Solid Phase Synthesis of N-Alkyl Sulfonamides

Synlett

Volumn 1997, Issue 7, 1997, Pages 854-856

  Dankwardt, Sharon M ^a   Smith, David B ^a   Porco Jr , John A ^b   Nguyen, Cindy H ^b  

^a ROCHE BIOSCIENCE   (United States)

^b Argonaut Technologies   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542639596     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5776     Document Type: Article

References (19)

1. Recent reviews on solid phase synthesis of small molecules: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 555-600. (b) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-54. (c) Fruechtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
2. Recent reviews on solid phase synthesis of small molecules: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 555-600. (b) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-54. (c) Fruechtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
3. Recent reviews on solid phase synthesis of small molecules: (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 555-600. (b) Hermkins, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-54. (c) Fruechtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
4. Polymer supported sulfonamides have been previously prepared: Gude, M.; Piarulli, U.; Potenza, D.; Salom, B.; Gennari, C. Tetrahedron Lett. 1996, 37, 8589-8592.
5. 2CN has been demonstrated (b) Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055-3056.
6. 2CN has been demonstrated (b) Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055-3056.
7. (a) Mitsunobu, O. Synthesis, 1981, 1.
8. (b) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 136.
9. α-Halomethyl sulfones are known to be unreactive towards intermolecular nucleophilic substitution due to steric hindrance see: Bordwell, F. G.; Cooper, G. D. J. Am. Chem. Soc. 1951, 73, 5184.
10. These compounds could form oxazolines under the basic reaction conditions see: Ganin, E. V.; Makarov, V. F.; Rozynov, B. V. Zh. Org. Khim. 1985, 21, 2411-15.
11. Percent purities are given by relative area percent product. HPLC's were run on a phenyl column, TFA in water (0.1%) - ACN gradient (5-90% ACN).
12. (a) Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34 , 1639-1642.
13. (b) Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Itô, S. Chemistry Lett. 1994, 539-542.
14. (a) Richter, L. S.; Gadek, T. R. Tetrahedron Lett. 1994, 35, 4705-4706.
15. (b) Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789-3792.
16. (c) Krchnak, V.; Flegelova, Z.; Weichsel, A. S.; Lebl, M. Tetrahedron Lett. 1995, 36, 6193-6196.
17. Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381-5382.
18. Stanley, M.; Tom, J. Y. K.; Burdick, D. J.; Struble, M.; Burnier, J. poster presentation at the 12th American Peptide Symposium 1991, Cambridge, MA.
19. Moran, E. J.; Wilson, T. E.; Cho, C. Y.; Cherry, S. G.; Schultz, P. G. Biopolymers 1995, 37, 213.