Arylsulfonate esters in solid phase organic synthesis. I. Cleavage with amines, thiolate, and imidazole

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 975-978

  Rueter, Jaimie K ^a   Nortey, Samuel O ^a   Baxter, Ellen W ^a   Leo, Gregory C ^a   Reitz, Allen B ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ARYLSULFONIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; RESIN; THIOL DERIVATIVE;

ARTICLE; DEGRADATION; ION EXCHANGE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032567966     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10719-5     Document Type: Article

References (25)

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18. 9. Amine libraries can also be prepared by conventional solution chemistry followed by removal of excess reagents by treatment with scavenger resins: (a) Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. J. Am. Chem. Soc. 1997, 119, 4874-4881.
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21. 2 (2X).
22. 13C NMR method.
23. 13. For a different 4-alkoxyphenyl sulfonyl resin attachment of a guanidine, see: Bonnat, M.; Bradley, M.; Kilburn, J. D. Tetrahedron Lett. 1996, 37, 5409-5412.
24. 2Cl functionality in the starting Merrifield resin.
25. 15. Parlow, J. J.; Naing, W.; South, M. S.; Flynn, D. L. Tetrahedron Lett. 1997, 38, 7959-7962. Although Parlow et al. use tetrafluorophthalic anhydride in their work, we found that phthalic anhydride works just as well for removal of dialkyl secondary amines from tertiary amines. Excess phthalic anhydride is hydrolyzed by the basic ion exchange resin, and the o-phthalic acid that is formed adheres to the resin.