A double decarboxylation reaction of an oxazolidinone and carboxylic acid: Its application to the synthesis of a new opioid lead compound

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 995-998

  Fujii, Hideaki ^a   Imaide, Satomi ^a   Watanabe, Akio ^a   Yoza, Kenji ^b   Nakajima, Mayumi ^c   Nakao, Kaoru ^c   Mochizuki, Hidenori ^c   Sato, Noriko ^a   Nemoto, Toru ^a   Nagase, Hiroshi ^a  

^a KITASATO UNIVERSITY   (Japan)

^b BRUKER AXS INC   (United States)

^c TORAY INDUSTRIES INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DECARBOXYLATION REACTIONS; OPIOID RECEPTORS; OXAZOLIDINONES; POTASSIUM CARBONATES;

CARBOXYLIC ACIDS; LEAD COMPOUNDS; OLEFINS; ORGANIC ACIDS; POTASSIUM; SYNTHESIS (CHEMICAL);

CARBOXYLATION;

15,16 NORNALTREXONE DERIVATIVE; ALKENE; CARBOXYLIC ACID; MU OPIATE RECEPTOR; NALTREXONE DERIVATIVE; OPIATE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; HYDROLYSIS; OZONOLYSIS; X RAY CRYSTALLOGRAPHY;

ANALGESICS, OPIOID; CARBOXYLIC ACIDS; CATALYSIS; DECARBOXYLATION; MOLECULAR STRUCTURE; OXAZOLIDINONES; RECEPTORS, OPIOID, MU; SPIRO COMPOUNDS;

EID: 75749131572     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9025463     Document Type: Article

References (40)

1. Dhawan, B. N.; Cesselin, F.; Reisine, T.; Bradley, P. B.; Portoghese, P. S.; Hamon, M. Pharmacol. Rev. 1996, 48, 567.
2. Fujii, H.; Nagase, H. Curr. Med. Chem. 2006, 13, 1109 and references therein.
3. κ agonists: (a) Kawai, K.; Hayakawa, J.; Miyamoto, T.; Imamura, Y.; Yamane, S.; Wakita, H.; Fujii, H.; Kawamura, K.; Matsuura, H.; Izumimoto, N.; Kobayashi, R.; Endo, T.; Nagase, H. Bioorg. Med. Chem. 2008, 16, 9188.
4. (b) Nemoto, T.; Fujii, H.; Narita, M.; Miyoshi, K.; Nakamura, A.; Suzuki, T.; Nagase, H. Bioorg. Med. Chem. Lett. 2008, 18, 6398.
5. (c) Nagase, H.; Watanabe, A.; Nemoto, T.; Yamaotsu, N.; Hayashida, K.; Nakajima, M.; Hasebe, K.; Nakao, K.; Mochizuki, H.; Hirono, S.; Fujii, H. Bioorg. Med. Chem. Lett. 2010, 20, 121.
6. δ agonists: (a) Nagase, H.; Kawai, K.; Hayakawa, J.; Wakita, H.; Mizusuna, A.; Matsuura, H.; Tajima, C.; Takezawa, Y.; Endoh, T. Chem. Pharm. Bull. 1998, 46, 1695.
7. (b) Nagase, H.; Yajima, Y.; Fujii, H.; Kawamura, K.; Narita, M.; Kamei, J.; Suzuki, T. Life Sci. 2001, 68, 2227.
8. (c) Nagase, H.; Osa, Y.; Nemoto, T.; Fujii, H.; Imai, M.; Nakamura, T.; Kanemasa, T.; Kato, A.; Gouda, H.; Hirono, S. Bioorg. Med. Chem. Lett. 2009, 19, 2792.
9. A putative ε agonist: Fujii, H.; Narita, M.; Mizoguchi, H.; Murachi, M.; Tanaka, T.; Kawai, K.; Tseng, L. F.; Nagase, H. Bioorg. Med. Chem. 2004, 12, 4133.
10. (a) Fujii, H.; Hirano, N.; Uchiro, H.; Kawamura, K.; Nagase, H. Chem. Pharm. Bull. 2004, 52, 747.
11. (b) Watanabe, A.; Kai, T.; Nagase, H. Org. Lett. 2006, 8, 523.
12. (c) Osa, Y.; Ida, Y.; Furuhata, K.; Nagase, H. Heterocycles 2006, 69, 271.
13. (d) Nagase, H.; Watanabe, A.; Nemoto, T.; Yamamoto, N.; Osa, Y.; Sato, N.; Yoza, K.; Kai, T. Tetrahedron Lett. 2007, 48, 2547.
14. (e) Nemoto, T.; Fujii, H.; Sato, N.; Nagase, H. Tetrahedron Lett. 2007, 48, 7413.
15. (f) Fujii, H.; Imaide, S.; Watanabe, A.; Nemoto, T.; Nagase, H. Tetrahedron Lett. 2008, 49, 6293.
16. (g) Nagase, H.; Watanabe, A.; Harada, M.; Nakajima, M.; Hasebe, K.; Mochizuki, H.; Yoza, K.; Fujii, H. Org. Lett. 2009, 11, 539.
17. (h) Fujii, H.; Ogawa, R.; Ohata, K.; Nemoto, T.; Nakajima, M.; Hasebe, K.; Mochizuki, H.; Nagase, H. Bioorg. Med. Chem. 2009, 17, 5983.
18. (i) Fujii, H.; Watanabe, A.; Nemoto, T.; Narita, M.; Miyoshi, K.; Nakamura, A.; Suzuki, T.; Nagase, H. Bioorg. Med. Chem. Lett. 2009, 19, 438.
19. (a) Beckett, A. H.; Casy, A. F. J. Pharm. Pharmacol. 1956, 6, 986.
20. (b) Beckett, A. H. J. Pharm. Pharmacol. 1956, 8, 848.
21. (c) Casy, A. F.; Parfitt, R. T. In Opioid Analgesics, Chemistry and Receptors; Plenum Press: NewYork, 1986; pp 473-475.
22. Imaide, S.; Fujii, H.; Watanabe, A.; Nemoto, T.; Nakajima, M.; Nakao, K.; Mochizuki, H.; Nagase, H. Bioorg. Med. Chem. Lett. DOI 10.1016/j.bmcl.2009.12.039.
23. Bal, B. S.; Childers, W. E. Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
24. Hara, S.; Taguchi, H.; Yamamoto, H.; Nozaki, H. Tetrahedron Lett. 1975, 16, 1545.
25. The thermal decarboxylation of a β-lactone has been widely used for preparation of an olefin. (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441.
26. (b) Rayner, C. M. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 1, pp 673-718.
27. Recent examples of the thermal decarboxylation of β-lactones: (a) Braun, N. A.; Meier, M.; Schmaus, G.; Hölscher, B.; Pickenhagen, W. Helv. Chim. Acta 2003, 86, 2698.
28. (b) Merlic, C. A.; Doroh, B. C. J. Org. Chem. 2003, 68, 6056.
29. (c) Buckle, M. J. C.; Fleming, I.; Gil, S.; Pang, K. L. C. Org. Biomol. Chem. 2004, 2, 749.
30. (d) Shindo, M.; Matsumoto, K.; Shishido, K. Chem. Commun. 2005, 2477.
31. (e) Shindo, M.; Matsumoto, K.; Shishido, K. Tetrahedron 2007, 63, 4271.
32. Olefins have been prepared by elimination reaction in which oxazolidinone functioned as a leaving group. (a) Danishefsky, S. J.; Panek, J. S. J. Am. Chem. Soc. 1987, 109, 917.
33. (b) Gates, K. S.; Silverman, R. B. J. Am. Chem. Soc. 1989, 111, 8891.
34. (c) Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735.
35. Another possible mechanism is discussed in the Supporting Information.
36. Some examples of syn elimination have been reported in molecules in which β-hydrogen and leaving group could not achieve an antiperiplanar conformation. Smith, M. B.; March, J. In March's Advanced Organic Chemistry; 6th ed.; John Wiley & Sons: New York, 2007; pp 1482-1483 and references therein.
37. In cyclic systems, the extent of anti and syn elimination depends on ring size. Cyclohexyl systems have a very strong preference for anti elimination. (a) Carey, F. A.; Sundberg, R. J. In Advanced Organic Chemistry, Part A: Structure and Mechanisms; 5th ed.; Springer: New York, 2007; p 559.
38. (b) See also ref 15.
39. Clayden, J.; Greeves, N.; Warren, S.; Wother, P. In Organic Chemistry; Oxford University Press: New York, 2001; pp 496-497.
40. Determination of the stereochemistries of compounds 15 and 16 is described in the Supporting Information.