A Consolidated and Continuous Synthesis of Ciprofloxacin from a Vinylogous Cyclopropyl Amide

Ciprofloxacin is a broad-spectrum antibiotic that is recognized as one of the World Health Organization’s Essential Medicines. It is particularly effective in the treatment of Gram-negative bacterial infections associated with urinary, respiratory, and gastrointestinal tract infections. A streamline...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-03, Vol.84 (6), p.3370-3376
Main Authors: Tosso, N. Perrer, Desai, Bimbisar K, De Oliveira, Eliseu, Wen, Juekun, Tomlin, John, Gupton, B. Frank
Format: Article
Language:English
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Summary:Ciprofloxacin is a broad-spectrum antibiotic that is recognized as one of the World Health Organization’s Essential Medicines. It is particularly effective in the treatment of Gram-negative bacterial infections associated with urinary, respiratory, and gastrointestinal tract infections. A streamlined and high yielding continuous synthesis of ciprofloxacin has been developed, which employs a chemoselective C-acylation step that precludes the need for intermediate isolations, extractions, or purifications. The end-to-end process has a residence time of 4.7 min with a 15.8 g/h throughput at laboratory scale and an overall isolated yield of 83%.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03222