Solid phase synthesis of olefin and hydroxyethylene peptidomimetics

Journal of the American Chemical Society

Volumn 118, Issue 48, 1996, Pages 12246-12247

  Rotella, David P ^a  

^a CEPHALON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030470056     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962290i     Document Type: Article

References (22)

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3. Campbell, D. A.; Bermak, J. C.; Burkoth, T. S.; Patel, D. V. J. Am. Chem. Soc. 1995, 117, 5381-5382.
4. Olefin isosteres: (a) Spatola, A. F. Chemistry and Biochemistry of Amino Acids Peptides and Proteins; Marcel Dekker: New York, 1983; Vol. 7, pp 267-357.
5. (b) Fujii, N.; Nakai, K.; Tamamura, H.; Otaka, H.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1995, 1359-1371. Hydroxyethylene isosteres:
6. (a) Abdel-Meguid, S. Med. Res. Rev. 1993, 13, 731-778.
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13. See the Supplementary Information for details.
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20. D values and NMR spectra for these alcohols are not reported in this work. Ocain and Rich (J. Med. Chem. 1988, 31, 2193-2199) also disclose this structure but give no physical characterization.
21. Aldrich, Catalog # 27021-0.
22. Examination of the resin by FTIR following cleavage indicates that all of the material has been cleaved in both sequences. The benzyl urethane linker appears to be somewhat unstable to m-chlorobenzoic acid generated as a result of olefin epoxidation of a structurally unrelated series of molecules being studied in these laboratories, based on FTIR analysis of the resin following the reaction and mass recovery following TFA cleavage.