Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Method for the Oxazolidinone Key Intermediate of Linezolid and its Formal Synthesis

  • Park, Hoon-Gyu (Department of Applied Chemistry, College of Applied Sciences, Kyung Hee University) ;
  • Kim, Bo-Jung (Department of Applied Chemistry, College of Applied Sciences, Kyung Hee University) ;
  • Bae, Dae-Il (Department of Applied Chemistry, College of Applied Sciences, Kyung Hee University) ;
  • Lim, Byung-Jo (Department of Applied Chemistry, College of Applied Sciences, Kyung Hee University) ;
  • Ko, Mi-Sun (Department of Applied Chemistry, College of Applied Sciences, Kyung Hee University) ;
  • Oh, Se-Han (Department of Applied Chemistry, College of Applied Sciences, Kyung Hee University) ;
  • Kim, Hak-Won (Department of Applied Chemistry, College of Applied Sciences, Kyung Hee University)
  • Received : 2011.12.30
  • Accepted : 2012.01.26
  • Published : 2012.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Gregory, W. A. U.S. Patent, 4,705,799, November 10, 1987.
  2. Gregory, W. A; Brittelli, D. R.; Wang, C.-L.; Wuonola, M. A.; McRipley, R. J.; Eustice, D. C.; Eberly, V. S.; Bartholomew, P. T.; Slee, A. M.; Forbes, M. J. Med. Chem. 1989, 32, 1673. https://doi.org/10.1021/jm00128a003
  3. Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673. https://doi.org/10.1021/jm9509556
  4. Shinabarger, D. I.; Marotti, K. R.; Murray, R. W.; Lin, A. H.; Melchior, E. P.; Swaney, S. M.; Dunyak, D. S.; Demyan, W. F.; Buysse, J. M. Antimicrob. Agents Chemother. 1997, 41, 2132.
  5. Grega, K. C.; Barbachyn, M. R.; Brickner, S. J.; Mizsak, S. A. J. Org. Chem. 1995, 60, 5255. https://doi.org/10.1021/jo00121a050
  6. Tucker, J. A.; Allwine, D. A.; Grega, K. C.; Barbachyn, M. R.; Klock, J. L.; Adamski, J. L.; Brickner, S. J.; Hutchinson, D. K.; Ford, C. W.; Zurenko, G. E.; Conradi, R. A.; Burton, P. S.; Jensen, R. M. J. Med. Chem. 1998, 41, 3727. https://doi.org/10.1021/jm980274l
  7. Wang, C.-L.; Gregory, W. A.; Wuonola, M. A. Tetrahedron 1989, 45, 1323. https://doi.org/10.1016/0040-4020(89)80130-9
  8. Reddy, G.M.; Ramulu, A.; Reddy, P. P. Lett. Org. Chem. 2010, 7, 45. https://doi.org/10.2174/157017810790533878
  9. Babu, K. C.; Reddy, R. B.; Gangaiah, L. Madhusudhan, G.; Mukkanti, K. Der Parma Chemica 2011, 3, 219.
  10. Kim, C.; Ko, S.Y. Bull. Korean Chem. Soc. 2011, 32, 4450 https://doi.org/10.5012/bkcs.2011.32.12.4450
  11. Langlois, N.; Moro, A. Eur. J. Org. Chem. 1999, 12, 3483.
  12. Langlois, N. Tetrahedron Lett. 1999, 40, 8801. https://doi.org/10.1016/S0040-4039(99)01873-0
  13. Onishi, T.; Hirose, N.; Otake, Y.; Nakano, T.; Honda, Y.; Nakazawa, M.; Izawa, K. EP 1081133 A1.
  14. Crimmins, M. T.; Tabet, E. A. J. Org. Chem. 2001, 66, 4012. https://doi.org/10.1021/jo015568k
  15. Onishi, T.; Hirose, N.; Otake, Y.; Nakano, T.; Honda, Y.; Nakazawa, M.; Izawa, K. EP 1428818 A2.
  16. Arasappan, A.; Njorge, F. G.; Bennett, F.; Girijavallabhan, V. M.; Huang, Y.; Huelgas, R.; Piwinski, J. J.; Shin, N. Y.; Verma, V.; Velazquez, F. WO 2010022121 A1.
  17. Giorgi, G.; Guideri, L.; Ponticelli, F. Tetrahedron 2011, 67, 1463. https://doi.org/10.1016/j.tet.2010.12.031
  18. Klunder, M. K.; Onami, T.; Sharpless, K. B. J. Org. Chem. 1989, 54, 1295. https://doi.org/10.1021/jo00267a014
  19. Suryakiran, N.; Prabhakar, P.; Srikanth Reddy, T.; Rajesh, K.; Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 8039. https://doi.org/10.1016/j.tetlet.2006.09.081

Cited by

  1. Concise asymmetric synthesis of Linezolid through catalyzed Henry reaction vol.3, pp.47, 2012, https://doi.org/10.1039/c3ra45186k
  2. Regioselectivity of the trifluoroethanol-promoted intramolecular N-Boc-epoxide cyclization towards 1,3-oxazolidin-2-ones and 1,3-oxazinan-2-ones vol.18, pp.37, 2020, https://doi.org/10.1039/d0ob01698e