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Multi-step continuous flow synthesis of fluconazole

  • Judy Szeto
  • Vi-Anh Vu
  • Jeremiah P. Malerich
  • Nathan Collins
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Abstract

The development of a flow chemistry approach to the anti-fungal fluconazole is described. A continuous, two-reactor, three-step synthesis of fluconazole from 2-chloro-2′,4′-difluoroacetophenone was achieved with no intermediate purification. The synthesis has been successfully demonstrated on a Vapourtec commercial flow chemistry system.

Graphical abstract

Keywords

Fluconazole Corey-Chaykovsky epoxidation 1,2,4-triazole Friedel-crafts acylation Vapourtec 

Notes

Acknowledgements

This research was developed with funding from the Defense Advanced Research Projects Agency (DARPA, W911NF-16-C-0051). The views, opinions, and/or findings expressed are those of the author(s) and should not be interpreted as representing the official views or policies of the Department of Defense or the U.S. Government.

References

  1. 1.
    Becher R, Wirsel SG (2012) Appl Microbiol Biotechnol 95(4):825–840Google Scholar
  2. 2.
    Abe F, Usui K, Hiraki T (2009) Biochemistry 48(36):8494–8504Google Scholar
  3. 3.
    WHO Model List of Essential Medicines (20th list) http://www.who.int/medicines/publications/essentialmedicines/en/ Retrieved 27 February 2018
  4. 4.
    Wang Y, Bian C (2014) Asian J Chem 26(24):8593Google Scholar
  5. 5.
    Korwar S, Amir S, Tosso PN, Desai BK, Kong CJ, Fadnis S, Telang NS, Ahmad S, Roper TD, Gupton BF (2017) Eur J Org Chem 6495–6498Google Scholar
  6. 6.
    Yang Y, Gong Z, Yang K (2015) Preparation of fluconazole from epoxy chloropropane through addition reaction, oxidation, and Grignard reaction. Patent CN 104557747Google Scholar
  7. 7.
    Palomo Coll (1994) A Process for preparation of fluconazole. Patent ES 2049663Google Scholar
  8. 8.
    Wu C, Li X, Shi X, Shi Y, Wang M (2011). Zhongguo Yaowu Huaxue Zazhi 21(4):304Google Scholar

Copyright information

© Akadémiai Kiadó 2018

Authors and Affiliations

  • Judy Szeto
    • 1
  • Vi-Anh Vu
    • 1
  • Jeremiah P. Malerich
    • 1
  • Nathan Collins
    • 1
  1. 1.Biosciences DivisionSRI InternationalMenlo ParkUSA

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