European Journal of Chemistry

A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid

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Ranjith Siddaraj
Shivaraja Govindaiah
Raghu Ningegowda
Nanjunda Swamy Shivananju
Babu Shubha Priya

Abstract

A concise and efficient synthesis of linezolid and eperezolid were accomplished through a convergent scheme utilizing diverse reaction conditions. The synthesis demonstrates utility of a new approach to facilitate the expeditious construction of 3-aryl-5-(substituted methyl)-2-oxazolidinones and easier insertion of N-acetyl group. This new approach offers the possibility of accessing related 2-oxazolidinone members easily as well as making additional analogues of Linezolid. The adopted method afforded high purity and excellent yield compared to other existing synthetic methods. The compounds were successfully characterized by known spectroscopic techniques.


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Siddaraj, R.; Govindaiah, S.; Ningegowda, R.; Shivananju, N. S.; Priya, B. S. A Novel and Expeditious Synthesis of Oxazolidinone Drugs Linezolid and Eperezolid. Eur. J. Chem. 2018, 9, 353-359.

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References

[1]. Wallace, R. J. J.; Brown-Elliott, B. A.; Ward, S. C.; Crist, C. J.; Mann, L. B.; Wilson, R. W. Antimicrob. Agents Chemother. 2001, 45, 764-767.
https://doi.org/10.1128/AAC.45.3.764-767.2001

[2]. Peters, J.; Kondo, K.; Lee, R.; Lin, C.; Inderlied, C. J. Antimicrob. Chemother. 1995, 35, 675-679.
https://doi.org/10.1093/jac/35.5.675

[3]. Vardakas, K. Z.; Kioumis, I.; Falagas, M. E. Curr. Drug Metab. 2009, 10, 2-12.
https://doi.org/10.2174/138920009787048446

[4]. Potoski, B. A.; Adams, J.; Clarke, L.; Shutt, K.; Linden, P. K.; Baxter, C.; Pasculle, A. W.; Capitano, B.; Peleg, A. Y.; Szabo, D.; Paterson, D. L. Clin. Infect. Dis. 2006, 43, 165-171.
https://doi.org/10.1086/505114

[5]. Toh, S. M.; Xiong, L.; Arias, C. A.; Villegas, M. V.; Lolans, K.; Quinn, J.; Mankin, A. S. Mol. Microbiol. 2007, 64, 1506-1514.
https://doi.org/10.1111/j.1365-2958.2007.05744.x

[6]. Roehrig, S.; Straub, A.; Pohlmann, J.; Lampe, T.; Pernerstorfer, J.; Schlemmer, K. H. Reinemer, P.; Perzborn, E. J. Med. Chem. 2005, 48, 5900-5908.
https://doi.org/10.1021/jm050101d

[7]. Kalia, V.; Miglani, R.; Purnapatre, K. P.; Mathur, T.; Singhal, S.; Khan, S.; Voleti, S. R.;Upadhyay, D. J.; Saini, K. S.; Rattan, A.; Raj, V. S. Antimicrob. Agents Chemother. 2009, 53, 1427-1433.
https://doi.org/10.1128/AAC.00887-08

[8]. Howe, R. A.; Wootton, M.; Noel, A. R.; Bowker, K. E.; Walsh, T. R.; MacGowan, A. P. Antimicrob. Agents Chemother. 2003, 47, 3651-3652.
https://doi.org/10.1128/AAC.47.11.3651-3652.2003

[9]. Livermore, D. M.; Mushtaq, S.; Warner, M.; Woodford, N. J. Antimicrob. Chemother. 2009, 63, 713-715.
https://doi.org/10.1093/jac/dkp002

[10]. Skripkin, E.; McConnell, T. S.; DeVito, J.; Lawrence, L.; Ippolito, J. A.; Duffy, E. M.; Sutcliffe, J.; Franceschi, F. Antimicrob. Agents Chemother. 2008, 52, 3550-3557.
https://doi.org/10.1128/AAC.01193-07

[11]. 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, 673-679.
https://doi.org/10.1021/jm9509556

[12]. Barbachyn, M. R.; Brickner, S. J.; Hutchinson, D. K. U.S. patent 5688792; 1997; Chem. Abstr. 1995, 123, 256742.

[13]. Dhananjay, G. S.; Nandu, B. B.; Avinash, V. N.; Kamlesh, D. S.; Anindya, S. B.; Tushar, A. N. PCT Int. Appl. 063505,2009; Chem. Abstr. 2009, 150, 515152.

[14]. Imbordino, R. J.; Perrault, W. R.; Reeder, M. R. PCT Int. Appl. 116284, 2007; Chem. Abstr. 2007, 147, 469356.

[15]. Pearlman, B. A.; Perrault, W. R.; Barbachyn, M. R.; Manninen, P. R.; Toops, D. S.; Houser, D. J.; Fleck, T. J. U.S. Patent 5837870, 1998; Chem. Abstr. 1998, 130, 25061.

[16]. Perrault, W. R.; Pearlman, B. A.; Godrej, D. B.; Jeganathan, A.;Yamagata, K.; Chen, J. J.; Lu, C. V.; Herrinton, P.M.; Gadwood, R. C.; Chan, L.; Lyster, M. A.; Maloney, M. T.; Moeslein, J. A.; Greene, M. L.; Barbachyn, M. R. Org. Proc. Res. Dev. 2003, 7, 533-546.
https://doi.org/10.1021/op034028h

[17]. Yu, D. S.; Huang, L.; Liang, H.; Gong, P. Chin. Chem. Lett. 2005, 16, 875-878.

[18]. Pearlman, B. A. PCT Int. Appl. 9924393, 1999; Chem. Abstr. 1999, 130, 338099.

[19]. Wang, M.; Tong, H. CN patent 101220001, 2008.

[20]. Mohan-Rao, D.; Krishna, R. P. PCT Int. Appl. 099353, 2005; Chem. Abstr. 2005, 143, 440395.

[21]. Mohan-Rao, D.; Krishna, R. P. PCT Int. Appl. 008754, 2006; Chem. Abstr. 2006, 144, 170978.

[22]. Madhusudhan, G.; Om Reddy, G.; Ramanatham, J.; Dubey, P. K. Indian J. Chem. 2005, 44B, 1236-1238.

[23]. Madhusudhan, G.; Om Reddy, G.; Rajesh, T.; Ramanatham, J.; Dubey, P. K. Tetrahedron Lett. 2008, 49, 3060-3062.
https://doi.org/10.1016/j.tetlet.2008.03.061

[24]. Rajesh, T.; Narayana Rao, S. P.; Suresh, K. Madhusudhan, G.; Mukkanti, K. J. Hetercyclic Chem. 2010, 47, 1392-1397.
https://doi.org/10.1002/jhet.494

[25]. Moran-Ramallal, R.; Liz, R.; Gotor, V. Org. Lett. 2008, 10, 1935-1938.
https://doi.org/10.1021/ol800443p

[26]. Mallesham, B.; Rajesh, B. M.; Rajamohan, R. P.; Srinivas, D.; Sanjay, T. Org. Lett. 2003, 5, 963-965.
https://doi.org/10.1021/ol026902h

[27]. Selvakumar, N.; Srinivas, D.; Manoj, K. K.; Sitaram, K. M.; Mamidi, R. N. V. S.; Hemanth, S.; Chandrashekar, C.; Srinivasa Rao, B.; Mohammed, R. A.; Jagattaran, D.; Javed, I.; Raagopalan, R. J. Med. Chem. 2002, 45, 3953-3962.
https://doi.org/10.1021/jm020092y

[28]. Tokuyama, R.; Takahashi, Y.; Tomita, Y.; Tsubouchi, M.; Yoshida, T.; Iwasaki, N.; Kado, N.; Okezaki, E.; Nagata, O. Chem. Pharm. Bull. 2001, 49, 361-367.
https://doi.org/10.1248/cpb.49.361

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