Generation of a piperazine-2-carboxamide library: A practical application of the phenol-sulfide react and release linker

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1295-1298

  Breitenbucher, J Guy ^a   Johnson, Charles R ^a   Haight, Mathew ^a   Phelan, J Christopher ^a  

^a Arris Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; PHENOL; PIPERAZINE DERIVATIVE;

ARTICLE; SYNTHESIS;

EID: 0032510277     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10870-X     Document Type: Article

References (19)

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2. 1. Backes, B.J.; Virgilio, A.A.; Ellman, J.A. J. Am. Chem. Soc. 1996, 118, 3055. Backes, B.J.; Ellman, J.A. J. Am. Chem. Soc. 1994, 116, 11171. Kenner, G.W.; McDermott, J.R.; Sheppard, R.C. J. Chem. Soc. Chem. Comm. 1971, 636. Osapay, G.; Taylor, J.W. J. Am. Chem. Soc. 1990, 112, 6046. Degrado, W.F.; Kaiser, E.T. J. Org. Chem. 1980, 45, 1295. Voyer, N.; Lavoie, A.; Pinette, M.; Bernier, J.Tetrahedron Lett. 1994, 35, 355.
3. 1. Backes, B.J.; Virgilio, A.A.; Ellman, J.A. J. Am. Chem. Soc. 1996, 118, 3055. Backes, B.J.; Ellman, J.A. J. Am. Chem. Soc. 1994, 116, 11171. Kenner, G.W.; McDermott, J.R.; Sheppard, R.C. J. Chem. Soc. Chem. Comm. 1971, 636. Osapay, G.; Taylor, J.W. J. Am. Chem. Soc. 1990, 112, 6046. Degrado, W.F.; Kaiser, E.T. J. Org. Chem. 1980, 45, 1295. Voyer, N.; Lavoie, A.; Pinette, M.; Bernier, J.Tetrahedron Lett. 1994, 35, 355.
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12. 13C-NMR, and MS.
13. 7. Resin purchased from Nova Biochem (1.34 meq/g).
14. 2. The resin was washed and dried providing 80g of Phenolsulfide resin. The phenol-sulfide loading was determined by elemental analysis for sulfur to be 98%.
15. 9. Yager, K.; Fantauzzi, P. Tetrahedron Lett. 1998, 39, 1291-1294.
16. 2, The presence of a purple color on the resin is indicative of phenol.
17. 11. Charles R. Johnson, Birong Zhang, Pascal Fantauzzi, Michael Hocker, Kraig Yager, Fifth International Symposium, Solid Phase Synthesis & Combinatorial Chemical Libraries, September 1997, London, UK.
18. 12. Hydromatrix® and ChemElut® are available from Varian Sample Preparation Products, CA.
19. 13. Correspondence regarding Solid Supported Liquid Extraction should be addressed to Charles R. Johnson.