AMEBA: An acid sensitive aldehyde resin for solid phase synthesis

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7151-7154

  Fivush, Adam M ^a   Willson, Timothy M ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; CARBAMIC ACID DERIVATIVE; SULFONAMIDE; UREA DERIVATIVE;

AMINATION; ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030658101     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01771-1     Document Type: Article

References (11)

1. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1997, 53, 5643-5678.
2. Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
3. Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007.
4. Ngu, K.; Patel, D. V. Tetrahedron Lett. 1997, 38, 973-976.
5. Wang, S. W. J. Am. Chem. Soc. 1973, 95, 1328-1333.
6. Mergler, M.; Nyfeler, R.; Gostelli, J.; Grogg, P. Chem. Biol., Proc. Am. Pept. Symp. 10th 1988, 259-260.
7. Chen, C; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661-2662.
8. Keifer, P. A. J. Org. Chem. 1996, 61, 1558-1559.
9. 2 generated the corresponding bromomethyl resin 6 (c.f. reference 4). In our hands, resin 6 was not stable to storage at room temperature and reaction with 4-methoxyphenethylamine gave variable results. (formula presented)
10. 2. Similar observations have prompted the generation of "super" acid labile linkers for traceless synthesis of secondary anilinoamides: a) Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742-5743.
11. b) Holmes, C. P., Presented at the 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997; paper ORGN 383.