A practical synthesis of N-Hydroxy-α-amino acid derivatives

Synthesis (Germany)

Volumn 1980, Issue 11, 1980, Pages 890-893

  Tijhuis, Marian W ^a   Herscheid, Jacobus D M ^a   Ottenheijm, Harry C J ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

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[No Author keywords available]

Indexed keywords

EID: 84988089697     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1980-29255     Document Type: Article

References (30)

1. P. G. Sammes, Progress in the Chemistry of Organic Natural Products, Vol. 32, W. Herz, H. Grisebach, G. W. Kirby, Eds., Springer Verlag, Heidelberg, Berlin, New York 1975, p. 93.
2. J. H. Weisburger, E. K. Weisburger, Pharmacol. Rev. 25, 1 (1973).
3. H. Maehr, Pure Appl. Chem. 28, 603 (1971).
4. J. B. Bapat, D. St. C. Black, R. F. C. Brown. Advances in Heterocyc/ic Chemistry, Vol. 10, A. R. Katritzky, A. J. Boulton, Eds., Academic Press, New York, London, 1969. p. 199.
5. J. B. Neilands, Science 156, 1443 (1967).
6. A. I. Scott, S. E. Yoo, S. K. Chung, J. A. Lacadie, Tetrahedron Lett. 1976, 1137.
7. U. Schmidt, J. Hausler, E. Ohler, H. Poisel in: Progress in the Chemistry of Organic Natural Products, Vol. 37, W. Herz, H. Grisebach, G. W. Kirby, Eds., Springer Verlag, Heidelberg, Berlin, New York, 1979, p. 251.
8. D. M. Herscheid, R. J. F. Nivard, M. W. Tijhuis, H. P. H. Scholten, H. C. J. Ottenheijm, J. Org. Chem. 45, 1880 (1980).
9. J. D. M. Herscheid, H. P. H. Scholten, M. W. Tijhuis, H. C. 1. Ottenheijm, Reel. Trav. Chim. Pays-Bas in press.
10. A. H. Cook, C. A. Slater, J. Chem. Soc. 1956, 4130.
11. L. Neelakantan, W. H. Hartung, J. Org. Chem. 23. 964 (1958).
12. E. Buehler, G. B. Brown, J. Org. Chem. 32, 265 (1967).
13. T. La Noce, E. Bellasio, E. Testa, Ann. Chim. (Rome) 58, 393 (1968).
14. A. Chimiak, Rocz. Chem. 42, 225 (1968).
15. T. Kolasa, A. Chimiak, Tetrahedron 30, 3591 (1974).
16. T. Polonski, A. Chimiak, J. Org. Chem. 41, 2092 (1976)
17. A. Ahmed, Bull. Chem. Soc. Jpn. 47, 1819, 2583 (1974).
18. B. L. Moller, I. J. McFarlane, E. E. Conn, Acta Chem. Scand. [B] 31, 343 1977).
19. J. D. M. Herscheid, H. C. J. Ottenheijm, Tetrahedron Lett. 1978, 5143.
20. This reagent has been used before for the reduction of oximes, see M. Kawase, Y. Kikugawa, J. Chem. Soc. Perkin Trans. I 1979. 643.
21. Y. Kikugawa, M. Kawase, Chem. Lett. 1977, 1279.
22. For a report on the acid-stability of amine/boranes sec: C. F. Lane, Aldrichimica Acta 6, 51 (1973).
23. Commercially available from Aldrich.
24. M. Akiyama, M. Hasegawa, H. Takeuchi, K. Shimizu, Tetrahedron Lett. 1979, 2599.
25. Except for the asparaginyl-glycine bond, peptide bonds are not attacked by hydroxylamine; see P. Bornstein, G. Balian in: Methods in Enzymology, Vol. 47, part E, C. H. W. Hirn, S. N. Timasheff, Eds., Academic Press, New York, London, 1 977, p. 132.
26. After completion of the manuscript, we became aware of two other methods, i. e. direct oxidation of peptides: S. A. Matlin, P. G. Sammes, R. M. Upton, J. Chem. Soc. Perkin Transl.1979, 2481
27. and addition of acid chlorides to oximes: V. J. Lee, R. B. Woodward, J. Org. Chem. 44, 2487 (1979).
28. The compounds can be isolated also by column chromatography under slightly increased pressure; however due to silica gelcatalyzed decomposition, yields are decreased then. This holds especially for compounds 7, the yields of which drop to about half of the values given, when usual column chromatography was used.
29. All compounds listed are new ones to our best knowledge; of 2b and 2f derivatives have been prepared before: see T. Polonski, A. Chimiak, J. Org. Chem. 41, 2092 (1976).
30. T. La Noce, E. Bellasia, E. Testa, Ann Chim. (Rome) 58, 393 (1968).