Arylsulfonate esters in solid phase organic synthesis. II. Compatibility with commonly-used reaction conditions

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 979-982

  Baxter, Ellen W ^a   Rueter, Jaimie K ^a   Nortey, Samuel O ^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; RESIN; SODIUM BOROHYDRIDE;

ACYLATION; AMINATION; ARTICLE; DEGRADATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0032567901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10718-3     Document Type: Article

References (13)

1. 1. Rueter, J. K.; Nortey, S. O.; Baxter., E. W.; Leo, G. C.; Reitz, A. B. Tetrahedron Lett., preceding paper in this issue.
2. 2OH was prepared by the method described in: Ackerley, N.; Brewster, A. G.; Brown, G. R.; Clarke, D. S.; Foubister, A. J.; Griffin, S. J.; Hudson, J. A.; Smithers, M. J.; Whittamore, P. R. O. J. Med. Chem. 1995, 38, 1608-1628.
3. 3. Zhong, H. M.; Greco, M. N.; Maryanoff, B. E. J. Org. Chem., in press.
4. 4. (a) Meyers, H. V.; Dilley, G. J.; Durgin, T. L.; Powers, T. S.; Winssinger, N. A.; Zhu, H.; Pavia, M. R. Molecular Diversity 1995, 1, 13-20.
5. (b) Lee, J. S.; Murray, W. V.; Rivero, R. A. J. Org. Chem. 1997, 62, 3874-3879.
6. 1
7. 1H NMR, MS, and TLC.
8. 2O at 220 nM with a photodiode array detector (for entries 10-14: 10, 86%; 11, 86%; 12, 74%; 13, 79%; 14, 68%). The major impurity observed by NMR was the carbonate salt of diethylamine, which could be suppressed by performing the reaction under inert atmosphere and working it up afterword in a timely manner.
9. 8. Vágner, J.; Krchnák, V.; Lebl, M.; Barany, B. Coll. Czech. Chem. Commun. 1996, 61, 1697-1702.
10. 9. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849-3862.
11. 10. Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. J. Org. Chem. 1996, 61, 6720-6722.
12. 11. Devraj, R.; Cushman, M. J. Org. Chem. 1996, 61, 9368-9373.
13. 12. Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 777, 11999.