Synthesis of a sterically congested α,α'-iminodiacid

Tetrahedron

Volumn 53, Issue 43, 1997, Pages 14591-14598

  Walker, Michael A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0030754986     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01065-X     Document Type: Article

References (31)

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3. Fushiya, S.; Matsuda, M; Yamada, S.; Nozoe, S. Tetrahedron 1996, 52, 877.
4. Nakashima, R.; Hayashi, N.; Mizutani, T.; Ueda, N.; Yamamoto, J.; Kimura, Y. Biosci. Biotechnol. Biochem. 1993, 57, 1514.
5. 2O, triflic anhydride.
6. (a) Gavras, H.; Biollaz, J.; Waeber, B.; Brunner, H. R.; Gavras, I.; Davies, R. D. The Lancet 1981, 543
7. (b) Chapman, K. T.; Kopka, I. E.; Durette, P. L.; Esser, C. K.; Lanza, T. J.; Izquierdo-Martin, M.; Niedzwiecki, L.; Chang, B.; Harrison, R. K.; Kuo, D. W.; Lin, T.-Y.; Stein, R. L.; Hagmann, W. K. J. Med. Chem. 1993, 36, 4293
8. (c) Baldwin, J. E.; Adlington, R. M.; Russell, A. T.; Smith, M. L. Tetrahedron 1995, 51, 4733.
9. (a) Cheng, S.; Tarby, C. M.; Comer, D. D.; Williams, J. P.; Caporale, L. H.; Myers, P. L.; Boger, D. L. Bioorg. Med. Chem. 1996, 4, 727.
10. (b) Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567.
11. Wong, S. S. Chemistry of Protein Conjugation and Crosslinking; CRC Press: Boca Raton, 1991.
12. A N-substituted 1'-carboxy-2'-methylpropyl)valine iminodiacid has been synthesized using the Ugi reaction. This reaction was selective for the R,S-diastereomer. See: (a) Yamada, T.; Motoyama, N.; Taniguchi, T.; Kazuta, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K.; Sugiura, M.; Chem. Lett., 1987, 723. However, the diastereoselectivity of the Ugi reaction can be controlled to yield iminodiacids having the S,S-configuration. See:
13. (b) Demharter, A.; Hörl, W.; Herdtweck, E.; Ugi, I. Angew. Chem. Int. Ed. 1996, 35, 173.
14. (c) Ugi, I.; Demharter, A.; Hörl, W.; Schmid, T. Tetrahedron 1996, 52, 11657.
15. In addition to the Ugi reaction (ref. 9), other methods have been reported for the synthesis of iminodiacids including: (a) modified Strecker conditions; Herranz, R.; Suárez-Gea, M. L.; Vinuesa, S.; García-López, M. T. J. Org. Chem. 1993, 58, 5186,
16. (b) reductive amination, Sangster, A. W.; Thomas, S. E.; Tingling, N. L. Tetrahedron 1975, 31 1135;
17. N2 reaction between α-aminoesters and α-bromo-or α-triflate-carboxylic acid esters, Effenberger, F.; Burkard, U. Liebegs Ann. Chem. 1986, 334.
18. Harfenist, M.; Hoeer, D. C.; Crouch, R. J. Org. Chem. 1983, 50, 1356, and
19. (d) α,α'-bis-alkylation of iminodiacetate, Einhorn, J.; Einhorn, C.; Pierre, J.-L. Synlett, 1994, 1023.
20. The (D)-enantiomer was chosen to take into account inversion at this center upon displacement of the triflate group.
21. Kogan, T. P.; Somers, T. C.; Venuti, M. C. Tetrahedron Lett. 1990, 46, 6623.
22. Effenberger, F.; Burkard, U.; Willfahrt, J. Angew. Chem., Int. Ed. 1983, 22, 65.
23. The analogous N-(1-carboxy-2-phenylethyl)phenyalanine iminodiacid was synthesized and found to be resistant to acylation as well.
24. The acylation of N-(carboxymethyl)alanine, N-(carboxymethyl)leucine and N-(carboxymethyl)valine esters is accomplished in high to low yield (respectively) at 10 kbar. Yamada, T.; Manabe, Y.; Miyazawa, T.; Kuwata, S.; Sera, A. Chem. Comm. 1984, 1500.
25. Kashima, C.; Harada, K. Perkin Trans, 1 1988, 1521.
26. The reaction was not successful without LiI.
27. The addition of base other than LiI to this reaction caused lactonization.
28. Walker, M. A. Tetrahedron Lett. 1994, 35, 665.
29. Unreacted maleimide and 10 were recovered from the reaction in 32% and 26% yield respectively. The rest of the reaction mixture consisted of a mixture of base-line (TLC) compounds which were not characterized.
30. The Mitsunobu reactions of alcohols of this type can lead to unexpected side reactions depending on the length of the tether linking the alcohol to the iminodiacid. For example see: Walker, M. A. Tetrahedron Lett. 1996, 37, 8133.
31. Tetrahedron, Vol. 53, No. 43, pp. 14547-14564, 1997