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

J Org Chem. 2019 Mar 15;84(6):3370-3376. doi: 10.1021/acs.joc.8b03222. Epub 2019 Mar 1.

Abstract

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%.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amides / chemistry*
  • Ciprofloxacin / chemical synthesis*
  • Ciprofloxacin / chemistry
  • Cyclopropanes / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • Amides
  • Cyclopropanes
  • Vinyl Compounds
  • Ciprofloxacin