Application of the Dakin-West reaction for the synthesis of oxazole-containing dual PPARα/γ agonists

Journal of Organic Chemistry

Volumn 68, Issue 7, 2003, Pages 2623-2632

  Godfrey, Alexander G ^a   Brooks, Dawn A ^a   Hay, Lynne A ^a   Peters, Mary ^a   McCarthy, James R ^a   Mitchell, David ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DAKIN-WEST REACTION;

SUPRAMOLECULAR CHEMISTRY;

SYNTHESIS (CHEMICAL);

AMINOMALONATE DERIVATIVE; ASPARTIC ACID; MALONIC ACID DERIVATIVE; OXAZOLE DERIVATIVE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; METABOLISM; POLYMERIZATION; SEQUENCE ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ASPARTIC ACID; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXAZOLES; RECEPTORS, CYTOPLASMIC AND NUCLEAR; TRANSCRIPTION FACTORS;

EID: 0037419327     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026655v     Document Type: Article

References (31)

1. (a) Brooks, D. A.; Etgen, G. J.; Rito, C. J.; Shuker, A. J.; Dominianni, S. J.; Warshawsky, A. M.; Ardecky, A.; Paterniti, J. R.; Tyhonas, J.; Karanewsky, D. S.; Kauffman, R. F.; Broderick, C. L.; Oldham, B. A.; Montrose-Rafizadeh, C.; Winneroski, L. L.; Faul, M. M.; McCarthy, J. R. J. Med. Chem. 2001, 44, 2061.
2. (b) Etgen, G. J.; Oldham, B. A.; Johnson, W. T., Broderick, C. L.; Brozinick, J. T.; Bean J. S.; Bensch, W. R.; Brooks, D. A.; Rito, C. J.; Shuker, A. J.; Kauffman, R. F. Diabetes 2002, 51, 1083.
3. (a) Issemann, I.; Green, S. Nature 1990, 347, 645.
4. (b) Mangelsdorf, D. J.; Evans, R. M. Cell 1995, 83, 841.
5. (c) Willson, T. M.; Brown, P. J.; Sterbach, D. D.; Henke, B. R. J. Med. Chem. 2000, 43, 527.
6. Auwerx, J. In Insulin Resistance, Metabolic Disease and Diabetic Complications: Proceedings of the 7th European Symposium on Metabolism, Padova, Sept 30-Oct 3, 1998; Elsevier: Amsterdam, 1999, p 167.
7. (a) Sohda, T.; Mizuno, K.; Momose, Y.; Ikeda, H.; Fujita, T.; Meguro, K. J. Med. Chem. 1992, 35, 2617.
8. (b) Hulin, B.; Clark, D. A.; Goldstein, S. W.; McDermott, R. E.; Dambek, P. J.; Kappeler, W. H.; Lamphere, C. H.; Lewis, D. M.; Rizzi, J. P. J. Med. Chem. 1992, 35, 1853.
9. (c) Lehmann, J. M.; Moore, L. B.; Smith-Oliver, T. A.; Wilkison, W. O.; Willson, T. M.; Kliewer, S. A. J. Biol. Chem. 1995, 270, 12953.
10. (d) Nomura, M.; Kinoshita, S.; Satoh, H.; Maeda, T.; Murakami, K.; Tsunoda, M.; Miyachi, H.; Awano, K. Bioorg. Med. Chem. Lett. 1999, 9, 533.
11. Fruchart, J.-C.; Duriez, P.; Staels, B. Curr. Opin. Lipidol. 1999, 10, 245.
12. (a) Dakin, H. D.; West, R. J. Biol. Chem. 1928, 91, 745.
13. (b) Buchanan, G. L. Chem. Soc. Rev. 1988, 17, 91.
14. (a) Robinson, R. J. Chem. Soc. 1909, 95, 2167.
15. (b) Gabriel, S. Chem. Ber. 1910, 43, 134, 1283.
16. Goto, Y.; Yamazaki, M.; Hamana, M. Chem. Pharm. Bull. 1971, 19, 2050.
17. Diacetyl monooxime, CAS [57-71-6], OHS Material Safety Data Sheet.
18. (a) Meguro, K.; Tawada, H.; Sugiyama, Y.; Fujita, T.; Kawamatsu, Y. Chem. Pharm. Bull. 1986, 34, 2840.
19. (b) Hulin, B.; Clark, D. A.; Goldstein, S. W.; McDermott, R. E.; Dambek, P. J.; Kappeler, W. H.; Lamphere, C. H.; Lewis, D. M.; Rizzi, J. P. J. Med. Chem. 1992, 35, 1853.
20. (c) Collins, J. L.; Blanchard, S. G.; Boswell, G. E.; Charifson, P. S.; Cobb, J. E.; Henke, B. R.; Hull-Ryde, E. A.; Kazmierski, W. M.; Lake, D. H.; Leesnitzer, L. M.; Lehmann, J.; Lenhard, J. M.; Orband-Miller, L. A.; Gray-Nunez, Y.; Parks, D. J.; Plunkett, K. D.; Tong, W.-Q. J. Med. Chem. 1998, 41, 5037.
21. (a) Sorensen, S. P. L. C. R. Trav. Lab. Carlsberg, Ser. Chim. 1903, 6,1.
22. (b) Sorensen, S. P. L.; Andersen, A. C. Z. Physiol. Chem. 1905, 44, 448.
23. (c) Sorensen, S. P. L. Z. Physiol. Chem. 1908, 56, 236.
24. The workup could be simplified by conducting the acylation step in the presence of PVP (4% cross-linked polyvinyl pyridine), which could be readily removed from the reaction mixture via filtration. Treatment of the ether-diluted filtrate with concentrated sulfuric acid (1 equiv) at room temperature for 2 h then provided direct formation of the oxazole product in yields comparable to the two-step procedure (40-50% following chromatography).
25. Kolb, M.; Barth, J.; Neises, B. Tetrahedron Lett. 1986, 27, 1579.
26. (a) Kawase, M. Heterocycles 1993, 36, 2441.
27. (b) Kawase, M.; Miyamae, H.; Kurihara, T. Chem. Pharm. Bull. 1998, 46, 749.
28. (c) Kawasi, M.; Miyamae, H.; Narita, M.; Kurihara, T. Tetrahedron Lett. 1993, 34, 859.
29. (d) Kawase, M. Tetrahedron Lett. 1994, 35, 149.
30. (a) Seki, M.; Kubota, H.; Moriya, T.; Yamagishi, M.; Nishimoto, S.; Matsumoto, K. Y. Chem. Pharm. Bull. 1986, 34, 4516.
31. (b) Hipskind, P. A.; Howbert, J.; Cho, S.; Cronin, J. S.; Fort, S. L.; Ginah, F. O.; Hansen, G. J.; Huff, B. E.; Lobb, K. L.; Martinelli, M. J.; Murray, A. R.; Nixon, J. A.; Staszak, M. A.; Copp, J. D. J. Org. Chem. 1995, 60, 7033.