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  • Synthesis: Ethyl N-allyl N-(3-fluoro-4-morpholinophenyl) carbamate
  • Introduction new ppt!

    1. 1. Synthesis of (±) - Linezolid Abhijeet Patil. M.Sc. Chemistry. Fergusson College, Pune.
    2. 2. INTRODUCTION <ul><li>Antibiotic – kills or inhibits growth of bacteria </li></ul><ul><li>Important for improving life expectancy of human population </li></ul><ul><li>To overcome drug resistance it is necessary to discover a new series of antibiotic classes </li></ul><ul><li>Hence, oxazolidinone (Linezolid) brought in clinical use </li></ul><ul><li>It has unique mode of action- inhibition of bacterial protein synthesis at early stage </li></ul><ul><li>Failure of penicillin and methicillin led to the invention of Linezolid </li></ul>
    3. 3. Clinical Applications of Linezolid <ul><li>Skin infections </li></ul><ul><li>Nosocomial pneumonia </li></ul><ul><li>Liver diseases </li></ul><ul><li>Cure of Tuberculosis </li></ul>
    4. 4. Synthesis of (±) – Linezolid: Scheme
    5. 5. Synthesis: 3-Fluoro-4-morpholinylnitrobenzene
    6. 6. Synthesis: 3-Fluoro-4-morpholinylaniline
    7. 7. Synthesis: N-Carboethoxy-3-fluoro-4-morpholinylaniline
    8. 8. Synthesis: Ethyl N-allyl N-(3-fluoro-4-morpholinophenyl) carbamate
    9. 9. Synthesis: 5-(Iodomethyl)-3-(4-morpholinophenyl) oxazolidin-2-one The obtained iodolactone was unstable.
    10. 10. Synthesis: [N-3-(3-Fluoro-4-morphylinyl phenyl)-2-oxo-5-oxazolidinyl] methyl azide
    11. 11. Synthesis: (±) - LINEZOLID
    12. 12. CONCLUSION <ul><li>(±) – LINEZOLID was synthesized in 7 steps. </li></ul><ul><li>The intermediates obtained at each step was isolated, purified by </li></ul><ul><li>chromatographic techniques like Thin layer chromatography and Column </li></ul><ul><li>chromatography. </li></ul><ul><li>These intermediates were characterized by FT-IR, NMR ( 1 H) spectroscopy. </li></ul><ul><li>The purpose of undertaking this project was to get an experience in multi- </li></ul><ul><li>step organic synthesis using sophisticated techniques at N.C.L. </li></ul>
    13. 13. REFERENCES <ul><li>S.J. Brickner, D.K. Hutchinson, M.R. Barbachyn, P.R. Mannien, D.A. Ulanowicz, S.A. Garmon, K.C. Grega, D.S. Tropps, C.W. Ford and G.E. Zurenks, . J. Med. Chem . 1996 , 39 , 673-679. </li></ul><ul><li>Swartz, M.N. Hospital acquired Infections: Diseases with Increasingly Limited Therapies. Proc. Natl. Sci .U .S.A 1994, 91 , 2420-2427. </li></ul><ul><li>Boyce. J. M, Opal, S. M, Chow, J. W, Zervos. M. J, Potter-Bynos. G, Sherman C. B, Romulo. R. L, C Fortna. S; J. Clin. Microbiolol. 1994, 1148-1153. </li></ul><ul><li>Gregory. W. A, Britteli. D. R, Wang. C. L. ; Wuonola. M. A.; McRipley. R.J; Eustice, D. C; Bartholomew, P. T, Slee. A. M. Forbes, M; J. Med. Chem. 1989, 32, 1673-1681. </li></ul><ul><li>Wang, C. L. J. Gregory, W. A.; Wuonola; Tetrahedron. 1989, 1323-1326. </li></ul><ul><li>Iwakura, Y.; Izawa, S. I; J. Org. Chem. 1964, 29, 379. </li></ul>
    14. 14. <ul><li>Herweh, J.E.; Kauffmann, W. J; Tetrahedron. Lett. 1971, 809-812 </li></ul><ul><li>Blumberg, H. M.; Rimland, P; Carroll, D. J.; Terry, P.; Wachsmuth, I. K. </li></ul><ul><li>J. Infec. Dis, 1991, 163, 1279-1285. </li></ul><ul><li>Fugitt, R. B.; Luckenbaugh, R W. U.S. Patent No.4128654, Dec. 5, 1978. </li></ul><ul><li>Gregory, W. A; U.S. Patent No.4461773, July 24, 1984. </li></ul><ul><li>Gregory, W. A; U. S. Patent No. 4,705,799, Nov 10, 1987 </li></ul>
    15. 15. THANK YOU <ul><li>Dr. J. M. Gajbhiye. </li></ul><ul><li>Pankaj Mahajan. </li></ul><ul><li>Parimal Naik. </li></ul><ul><li>Dr.M.N.Deshmukh . </li></ul>

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