AMD070, a CXCR4 Chemokine Receptor Antagonist: Practical Large-Scale Laboratory Synthesis
Organic Process Research & Development2008Vol. 12(5), pp. 823–830
Citations Over TimeTop 20% of 2008 papers
Jason Crawford, Gang Chen, David T. Gauthier, Trevor Wilson, Bryon Carpenter, Ian R. Baird, Ernest J. McEachern, Alan Matthew Kaller, Curtis Harwig, Bem Atsma, Renato T. Skerlj, Gary Bridger
Abstract
An efficient and convergent four-step synthetic route to the CXCR4 chemokine receptor antagonist AMD070 (1) has been developed which employs only a single chromatographic step in the entire sequence. Novel reductive amination methods have been developed for the coupling of 2 and 3 in which a dehydrative imine formation is followed by reduction with an attenuated borohydride reagent (zinc chloride and sodium borohydride). Selective extraction methods were employed to purify synthetic intermediates and remove reagents and impurities. A procedure has also been developed to isolate 1 in a pure crystalline form.
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