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A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow
Author(s) -
Lin Hongkun,
Dai Chunhui,
Jamison Timothy F.,
Jensen Klavs F.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703812
Subject(s) - ciprofloxacin hydrochloride , ciprofloxacin , acylation , dimethylamine , chemistry , yield (engineering) , sequence (biology) , hydrochloride , continuous flow , chromatography , organic chemistry , materials science , biochemistry , physics , antibiotics , mechanics , metallurgy , catalysis
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.