Facile preparationof chloromethylaryl solid supports using methanesulfonyl chloride and Hunig's base

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5789-5790

  Nugiel, David A ^a   Wacker, Dean A ^a   Nemeth, Gregory A ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RESIN;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030814063     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01029-0     Document Type: Article

References (12)

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2. Ellman, J.A. Acc. Chem. Res. 1996, 29(3), 132-43. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52(13), 4527-54. Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51(30), 8135-73. Gordon, E.M.; Barret, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A. J. Med. Chem. 1994, 37, 1233-51.
3. Ellman, J.A. Acc. Chem. Res. 1996, 29(3), 132-43. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52(13), 4527-54. Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51(30), 8135-73. Gordon, E.M.; Barret, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A. J. Med. Chem. 1994, 37, 1233-51.
4. Ellman, J.A. Acc. Chem. Res. 1996, 29(3), 132-43. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52(13), 4527-54. Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51(30), 8135-73. Gordon, E.M.; Barret, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A. J. Med. Chem. 1994, 37, 1233-51.
5. Mergler, M.; Nyfeler, R.; Gosteli, J. Tetrahedron Lett. 1989, 30, 6741-4 and 6745-8.
6. Wang, S.-W. J. Am. Chem. Soc. 1973, 95, 1328.
7. Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P. Tetrahedron Lett. 1988, 29, 4005.
8. Appel, R. Angew. Chem. 1975, 87, 863.
9. Inefficient removal of diisopropylethylamine hydrochloride would result in erroneous chlorine content determination. The lack of any elemental nitrogen indicates these salts were efficiently removed in the washing process.
10. No reaction was observed without prior drying of the resin.
11. Chlorine analysis allowed for conversion determination based on the initial resin loading level.
12. Holmes, C.R. et al J. Org. Chem. 1995, 60, 2318.