Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 30, Pages 8870-8873Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703812
Keywords
aromatic substitution; ciprofloxacin; continuous flow; multicomponent reactions; multistep synthesis
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Funding
- Defense Advanced Research Projects Agency (DARPA) [N666001-11-C-4005]
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Within a total residence time of 9 min, the sodium salt of ciprofloxacin was prepared from simple building blocks via a linear sequence of six chemical reactions in five flow reactors. Sequential offline acidifications and filtrations afforded ciprofloxacin and ciprofloxacin hydrochloride. The overall yield of the eight-step sequence was 60%. No separation of intermediates was required throughout the synthesis when a single acylation reaction was applied to remove the main byproduct, dimethylamine.
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