Synthesis of all distinct α-methyl-substituted isomers of amino bis(2,2'-ethanoic acid) diethyl ester and ethylene diamine tetraacetic acid tetraethyl ester scaffolds

Tetrahedron

Volumn 56, Issue 16, 2000, Pages 2359-2367

  Insaf, Shabana S ^a   Witiak, Donald T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Alkylation; Amines; Stereoisomerism

Indexed keywords

ACETIC ACID ESTER; EDETIC ACID DERIVATIVE; ESTER; METHYL GROUP;

ARTICLE; ENZYME INHIBITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

EID: 0034646889     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00103-4     Document Type: Article

References (64)

1. (a) Baker, W.; Fung, A.; Kleinert, H.; Stein, H.; Plattner, J.; Armiger, Y.-L.; Condon, S.; Cohen, J.; Egan, D.; Barlow, J.; Verburg, K.; Martin, D.; Young, G.; Polakowski, J.; Boyd, S.; Perun, T. J. Med. Chem. 1992, 35, 1722-1734.
2. (b) Barton, J.; Piwinski, J.; Skiles, J. W.; Regan, J. R.; Menard, P. R.; Desai, R.; Golec, F. S.; Reilly, L. W.; Goetzen, T.; Ueng, S.-N.; Warus, J. D.; Schwab, A.; Samuels, A. I.; Neiss, E. S.; Suh, J. T. J. Med. Chem. 1990, 33, 1600-1606.
3. (c) Kogan, T. P.; Rawson, T. E. Tetrahedron Lett. 1992, 33, 7089-7092.
4. Martin, H.; Gysin, H. US 2411662, 1946, pp 12.
5. Singh B.S. Tetrahedron Lett. 36:1995;2009-2012.
6. Mickelson J.W., Belonga K.L., Jacobsen E.J. J. Org. Chem. 60:1995;4177.
7. Harfenist M., Hoerr D.C., Crouch R. J. Org. Chem. 50:1985;1356.
8. Kasina S., Fritzberg A.R., Johnson D.L., Eshima D.J. J. Med. Chem. 29:1986;1933.
9. Lehn J.-M. Acc. Chem. Res. 11:1978;49.
10. Popter A.E.A. Katritzky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry. Vol. 3:1984;179 Pergamon, Oxford.
11. (a) Mukkala, V.-M.; Kwiatkowski, M.; Kankare, J.; Takalo, H. Helv. Chim. Acta 1993, 76, 893-899.
12. (b) Ruan, F.; Chen, Y.; Hopkins, P. J. Am. Chem. Soc. 1990, 112, 9403-9404.
13. (c) Ruan, F.; Chen, Y.; Itoh, K.; Sasaki, T.; Hopkins, P. J. Org. Chem. 1991, 56, 4347-4354.
14. (d) Martin, V.; Keanna, J. Synth. Commun. 1995, 25, 3625-3634.
15. (e) Storrs, R.; Tropper, F.; Li, H.; Song, C.; Kuniyoshi, J.; Sipkins, D.; Li, K.; Bednarski, M. J. Am. Chem. Soc. 1995, 117, 7301-7306.
16. (f) Xu, J.; Kullgren, B.; Durbin, P.; Raymond, K. J. Med. Chem. 1995, 38, 2606-2614.
17. (g) Sosnovsky, G.; Rao, N.; Li, S.; Swartz, H. J. Org. Chem. 1989, 54, 3667-3674.
18. (h) Goetz, C.; Debbrecht, F. Iowa State Coll. J. Sci. 1959, 33, 267-277.
19. (i) Eckelman, W.; Karesh, S.; Reba, R. J. Pharm. Sci. 1975, 64, 704-706.
20. (j) Gutsche, C.; Mei, G. J. Am. Chem. Soc. 1985, 107, 7964.
21. (k) Kahana, N.; Arad-Yellin, R.; Warshawsky, A. J. Org. Chem. 1994, 59, 4832-4837.
22. Dazzi, J. Swiss Patent 569,405, 1975, pp 9; Chem. Abstr. 1975, 84, 120434a.
23. (a) Daeid, N.; Nolan, K. B.; Ryan, L. J. Chem. Soc., Dalton Trans. 1991, 2301-2304.
24. (b) Herman, E. H.; Witiak, D. T.; Hellmann, K.; Waravdekar, V. S. Adv. Pharmacol. Chemother. 1982, 19, 249-290.
25. (c) Roca, J.; Ishida, R.; Berger, J.; Andoh, T.; Wang, J. C. Proc. Natl. Acad. Sci. USA 1994, 91, 1781-1785.
26. Garrigues B. Tetrahedron. 40:1984;1151-1156.
27. (a) Mukkala, V.-M.; Kwiatkowski, M.; Kankare, J.; Takalo, H. Helv. Chim. Acta 1993, 76, 893.
28. (b) Wolf, L.; Holzapfel, H. Chem. 1962, 2, 374.
29. (c) Shin, C.; Ohmatsu, H.; Sato, Y.; Yoshimura, J. Chem. Lett. 1981, 701.
30. (d) Kozikowski, A.; Tückmantel, W.; Liao, Y.; Manev, H.; Ikonomovic, S.; Wroblewski, J. J. Med. Chem. 1993, 36, 2706.
31. (e) Klutchko, S.; Blankley, J.; Fleming, R. W.; Hinkley, J.; Werner, A.; Nordin, I.; Holmes, A.; Hoefle, M.; Cohen, D.; Essenburg, A.; Kaplan, H. J. Med. Chem. 1986, 29, 1953.
32. (f) Johansen, J.; Christie, B.; Rapaport, H. J. Org. Chem. 1981, 46, 4914.
33. (g) Prota, G.; Ponsiglione, E. Tetrahedron 1973, 29, 4271.
34. (h) Singh, S. B. Tetrahedron Lett. 1995, 36, 2009.
35. (i) Insaf, S. S.; Witiak, D. T. Synthesis 1999, 435.
36. (a) Lillocci, C. J. Org. Chem. 1988, 53, 1733.
37. (b) Bottini, A. T.; Sousa, L. R.; Dowden, B. F. J. Org. Chem. 1974, 39, 355.
38. (c) Huh, N.; Thompson, C. M. Tetrahedron 1995, 51, 5935.
39. (d) Fry, E. M. J. Org. Chem. 1965, 30, 2058.
40. (e) Leonard, N. J.; Jann, K.; Paukstelis, J. V.; Steinhardt, C. K. J. Org. Chem. 1963, 28, 1499.
41. (f) Golumbig, C.; Fruton, J. S.; Bergmann, M. J. Org. Chem. 1946, 11, 518.
42. (g) Evans, D. A.; Mitch, C. H. Tetrahedron Lett. 1982, 23, 285.
43. (h) Trefonas, L. M.; Majeste, R. Tetrahedron 1963, 19, 929.
44. (i) Cohen, B.; Van Artsdalen, E. R.; Harris, J. J. Am. Chem. Soc. 1952, 8, 1875 and 1878.
45. (j) Leonard, N. J.; Jann, K. J. Am. Chem. Soc. 1962, 84, 4806.
46. (k) Di Vona, M.; Illuminati, G.; Lillocci, C. J. Chem. Soc., Chem. Commun. 1985, 7, 380.
47. (l) Rosen, G.; Ehrenpreis, S.; Mittag, T. J. Med. Chem. 1971, 14, 514.
48. (m) Cassinelli, A.; Angeli, P.; Giannella, M.; Gualtieri, F. Eur. J. Med. Chem. 1987, 22, 5.
49. (n) Hansen, B. Acta Chem. Scand. 1962, 16, 1945.
50. (o) Hall, A. W.; Taylor, R.; Simmonds, S. H.; Strange, P. G. J. Med. Chem. 1987, 30, 1879.
51. (p) Ringdahl, B.; Jenden, D. J. J. Med. Chem. 1987, 30, 852.
52. (q) Cohen, S. A.; Neumeyer, J. L. J. Med. Chem. 1983, 26, 1348.
53. (r) Foley, P. J.; Neale, R. J. Chem. Engng Data 1968, 13, 593.
54. (s) Di Vona, M.; Illuminati, G.; Lillocci, C. J. Chem. Soc., Perkin Trans. 2 1985, 1943.
55. (t) Gamcsik, M.; Hamhill, T. G.; Colvin, M. J. Med. Chem. 1990, 33, 1009.
56. (u) Ringdahl, B.; Mellin, C.; Ehlert, F.; Roch, M.; Rice, K.; Jenden, D. J. J. Med. Chem. 1990, 33, 281.
57. (v) Karton, Y.; Bradbury, B.; Baumgold, J.; Paek, R.; Jacobson, K. J. Med. Chem. 1991, 34, 2133.
58. (w) Golding, B.; Kebbell, M. J. J. Chem. Soc., Perkin Trans. 2 1987, 705.
59. (x) Liu, Q.; Simms, M.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1994, 1363.
60. (y) Chapman, N.; James, J. J. Chem. Soc. 1954, 2103.
61. (z) Hanby, W.; Hartley, G.; Powell, E.; Rydon, H. J. Chem. Soc. 1947, 519.
62. Walkowiak W., Ndip G.M., Desai D.H., Lee H., Bartsch R.A. Anal. Chem. 64:1992;1685-1690.
63. Yokoyama M., Nakao E., Sujino K., Watanabe S., Togo H. Heterocycles. 31:1990;1669-1685.
64. Another procedure for the syntheses of diastereomerically enriched mixtures of 7a+7c and 7b+7c is reported by: Harfenist, M., Hoerr, D. C., Crouch, R. J. Org. Chem. 1985, 50, 1356.