A facile synthesis of the oxazolidinone antibacterial agent linezolid

Yan-Wu Li Yan Liu Yun-Can Jia Jian-Yong Yuan

Citation:  Yan-Wu Li, Yan Liu, Yun-Can Jia, Jian-Yong Yuan. A facile synthesis of the oxazolidinone antibacterial agent linezolid[J]. Chinese Chemical Letters, 2013, 24(3): 230-232. shu

A facile synthesis of the oxazolidinone antibacterial agent linezolid

    通讯作者: Jian-Yong Yuan,
摘要: A facile synthetic route of linezolid 1 has been developed. Using commercially available (R)-epichlorohydrin as the starting material, 1 was obtained through a sequence of cyclization, substitution, a Goldberg coupling, aminolysis and acetylation reactions. The synthetic route is easy to perform and can be scaled up.

English

  • 
    1. [1] National Nosocomial Infections Surveillance (NNIS) System, National Nosocomial Infections Surveillance (NNIS) system report, data summary from January 1992 through June 2004, Am. J. Infect. Control. 32 (2004) 470-485.[1] National Nosocomial Infections Surveillance (NNIS) System, National Nosocomial Infections Surveillance (NNIS) system report, data summary from January 1992 through June 2004, Am. J. Infect. Control. 32 (2004) 470-485.

    2. [2] H. Goossens, European status of resistance in nosocomial infections, Chemotherapy 51 (2005) 177-181.[2] H. Goossens, European status of resistance in nosocomial infections, Chemotherapy 51 (2005) 177-181.

    3. [3] L.B. Rice, Antimicrobial resistance in gram-positive bacteria, Am. J. Infect. Control. 34 (Suppl. 5) (2006) S11-S19.[3] L.B. Rice, Antimicrobial resistance in gram-positive bacteria, Am. J. Infect. Control. 34 (Suppl. 5) (2006) S11-S19.

    4. [4] D.K. Hutchinson, Oxazolidinone antibacterial agents: a critical review, Curr. Top. Med. Chem. 3 (2003) 1021-1042.[4] D.K. Hutchinson, Oxazolidinone antibacterial agents: a critical review, Curr. Top. Med. Chem. 3 (2003) 1021-1042.

    5. [5] M.B. Gravestock, Recent developments in the discovery of novel oxazolidinone antibacterials, Curr. Opin. Drug Discov. Devel. 8 (2005) 469-477.[5] M.B. Gravestock, Recent developments in the discovery of novel oxazolidinone antibacterials, Curr. Opin. Drug Discov. Devel. 8 (2005) 469-477.

    6. [6] T.S. Lundstrom, J.D. Sobel, Antibiotics for gram-positive bacterial infections: vancomycin, quinupristin-dalfopristin, linezolid, and daptomycin, Infect. Dis. Clin. North Am. 18 (2004) 651-668.[6] T.S. Lundstrom, J.D. Sobel, Antibiotics for gram-positive bacterial infections: vancomycin, quinupristin-dalfopristin, linezolid, and daptomycin, Infect. Dis. Clin. North Am. 18 (2004) 651-668.

    7. [7] W.A. Gregory, D.R. Brittelli, C.L.J. Wang, et al., Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group, J. Med. Chem. 32 (1989) 1673-1681.[7] W.A. Gregory, D.R. Brittelli, C.L.J. Wang, et al., Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group, J. Med. Chem. 32 (1989) 1673-1681.

    8. [8] S.J. Brickner, D.K. Hutchinson, M.R. Barbachyn, et al., Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections, J. Med. Chem. 39 (1996) 673-679.[8] S.J. Brickner, D.K. Hutchinson, M.R. Barbachyn, et al., Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections, J. Med. Chem. 39 (1996) 673-679.

    9. [9] D. Yu, G. Huiyuan, A high yielding one-pot, novel synthesis of carbamate esters from alcohols using Mitsunobu's reagent, Bioorg. Med. Chem. Lett. 12 (2002) 857-859.[9] D. Yu, G. Huiyuan, A high yielding one-pot, novel synthesis of carbamate esters from alcohols using Mitsunobu's reagent, Bioorg. Med. Chem. Lett. 12 (2002) 857-859.

    10. [10] D.M. Rao, P.K. Reddy, Process for the preparation of linezolid and related compounds, WO 2005099353 A3 (2005).[10] D.M. Rao, P.K. Reddy, Process for the preparation of linezolid and related compounds, WO 2005099353 A3 (2005).

    11. [11] G. Madhusudhan, G.O. Reddy, J. Ramanatham, et al., A facile synthesis of 2-((5R)-2-oxo-5-oxazolidinyl)methyl-1H-isoindole-1,3(2H)-dione, Indian J. Chem. 45B (2006) 1264-1268.[11] G. Madhusudhan, G.O. Reddy, J. Ramanatham, et al., A facile synthesis of 2-((5R)-2-oxo-5-oxazolidinyl)methyl-1H-isoindole-1,3(2H)-dione, Indian J. Chem. 45B (2006) 1264-1268.

    12. [12] O.A. Phillips, E.E. Udo, M.E. Abdel-Hamid, et al., Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole) methyl oxazolidinones, Eur. J. Med. Chem. 44 (2009) 3217-3227.[12] O.A. Phillips, E.E. Udo, M.E. Abdel-Hamid, et al., Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole) methyl oxazolidinones, Eur. J. Med. Chem. 44 (2009) 3217-3227.

    13. [13] R.J. Sciotti, M. Pliushchev, P.E. Wiedeman, et al., The synthesis and biological evaluation of a novel series of antimicrobials of the oxazolidinone class, Bioorg. Med. Chem. Lett. 12 (2002) 2121-2123.[13] R.J. Sciotti, M. Pliushchev, P.E. Wiedeman, et al., The synthesis and biological evaluation of a novel series of antimicrobials of the oxazolidinone class, Bioorg. Med. Chem. Lett. 12 (2002) 2121-2123.

    14. [14] B. Mallesham, B.M. Rajesh, P.R. Reddy, et al., Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone, Org. Lett. 5 (2003) 963-965.[14] B. Mallesham, B.M. Rajesh, P.R. Reddy, et al., Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone, Org. Lett. 5 (2003) 963-965.

    15. [15] J.F. Hartwig, Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: scope and mechanism, Angew. Chem. Int. Ed. 37 (1998) 2046-2067.[15] J.F. Hartwig, Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates: scope and mechanism, Angew. Chem. Int. Ed. 37 (1998) 2046-2067.

    16. [16] J.P. Wolfe, S. Wagaw, J.F. Marcoux, et al., Rational development of practical catalysts for aromatic carbon-nitrogen bond formation, Acc. Chem. Res. 31 (1998) 805-818.[16] J.P. Wolfe, S. Wagaw, J.F. Marcoux, et al., Rational development of practical catalysts for aromatic carbon-nitrogen bond formation, Acc. Chem. Res. 31 (1998) 805-818.

    17. [17] A. Klapars, J.C. Antilla, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles, J. Am. Chem. Soc. 123 (2001) 7727-7729.[17] A. Klapars, J.C. Antilla, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles, J. Am. Chem. Soc. 123 (2001) 7727-7729.

    18. [18] A. Klapars, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides, J. Am. Chem. Soc. 124 (2002) 7421-7428.[18] A. Klapars, X. Huang, S.L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides, J. Am. Chem. Soc. 124 (2002) 7421-7428.

    19. [19] S.K. Kang, D.H. Kim, J.N. Park, Copper-catalyzed N-arylation of aryl iodides with benzamides or nitrogen heterocycles in the presence of ethylenediamine, Synlett (2002) 427-430.[19] S.K. Kang, D.H. Kim, J.N. Park, Copper-catalyzed N-arylation of aryl iodides with benzamides or nitrogen heterocycles in the presence of ethylenediamine, Synlett (2002) 427-430.

    20. [20] B. Mallesham, B.M. Rajesh, P. Rajamolhan Reddy, et al., Highly efficient CuIcatalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone, Org. Lett. 5 (2003) 963-965.[20] B. Mallesham, B.M. Rajesh, P. Rajamolhan Reddy, et al., Highly efficient CuIcatalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone, Org. Lett. 5 (2003) 963-965.

    21. [21] Y. Hayashi, T. Kayatani, H. Sugimoto, et al., Synthesis, characterization, and reversible oxygenation of alkoxo diiron(Ⅱ) complexes with the dinucleating ligand N,N,N0,N0-tetrakis{(6-methyl-2-pyridyl)methyl}-1,3-diamino-propan-2-olate, J. Am. Chem. Soc. 117 (1995) 11220-11229.[21] Y. Hayashi, T. Kayatani, H. Sugimoto, et al., Synthesis, characterization, and reversible oxygenation of alkoxo diiron(Ⅱ) complexes with the dinucleating ligand N,N,N0,N0-tetrakis{(6-methyl-2-pyridyl)methyl}-1,3-diamino-propan-2-olate, J. Am. Chem. Soc. 117 (1995) 11220-11229.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  0
  • HTML全文浏览量:  0
文章相关
  • 发布日期:  2013-03-07
  • 收稿日期:  2012-12-07
  • 网络出版日期:  2013-01-08
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章