A Concise Flow Synthesis of Efavirenz†

    Dr. Camille A. Correia1, Dr. Kerry Gilmore1, Prof. Dr. D. Tyler McQuade3, Prof. Dr. Peter H. Seeberger1 2 *

    • 1 Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam (Germany)
    • 2 Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin (Germany)
    • 3 Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306 (USA)

    Efavirenz is an essential medicine for the treatment of HIV, which is still inaccessible to millions of people worldwide. A novel, semi-continuous process provides rac-Efavirenz with an overall yield of 45 %. This streamlined proof-of-principle synthesis relies on the efficient copper-catalyzed formation of an aryl isocyanate and a subsequent intramolecular cyclization to install the carbamate core of Efavirenz in one step. The three-step method represents the shortest synthesis of this life-saving drug to date.

    We gratefully acknowledge generous financial support from the Max-Planck-Society. We also thank Vapourtec for lending us a fully equipped E-Series Flow System.

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