Literature DB >> 28561939

A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow.

Hongkun Lin1, Chunhui Dai2, Timothy F Jamison2, Klavs F Jensen1.   

Abstract

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.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aromatic substitution; ciprofloxacin; continuous flow; multicomponent reactions; multistep synthesis

Mesh:

Substances:

Year:  2017        PMID: 28561939     DOI: 10.1002/anie.201703812

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  12 in total

Review 1.  The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

2.  Electrochemical degradation of ciprofloxacin on BDD anode using a differential column batch reactor: mechanisms, kinetics and pathways.

Authors:  Guangchao Li; Shiqing Zhou; Zhou Shi; Xiaoyang Meng; Ling Li; Bin Liu
Journal:  Environ Sci Pollut Res Int       Date:  2019-04-27       Impact factor: 4.223

3.  Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks.

Authors:  Subbarao Yalamanchili; Tu-Anh Nguyen; Alexander Zsikla; Gavin Stamper; Ashley E DeYong; John Florek; Olivea Vasquez; Nicola L B Pohl; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-21       Impact factor: 16.823

4.  3D-Printed Labware for High-Throughput Immobilization of Enzymes.

Authors:  Michael B Spano; Brandan H Tran; Sudipta Majumdar; Gregory A Weiss
Journal:  J Org Chem       Date:  2020-06-17       Impact factor: 4.198

5.  Development and Scale-up of the Rapid Synthesis of Triphenyl Phosphites in Continuous Flow.

Authors:  Mengmei Mao; Le Zhang; Hanlin Yao; Li Wan; Zhong Xin
Journal:  ACS Omega       Date:  2020-04-17

6.  Chiral auxiliary recycling in continuous flow: automated recovery and reuse of Oppolzer's sultam.

Authors:  R J Sullivan; S G Newman
Journal:  Chem Sci       Date:  2018-01-25       Impact factor: 9.825

7.  Accelerated microfluidic native chemical ligation at difficult amino acids toward cyclic peptides.

Authors:  Nathalie Ollivier; Thomas Toupy; Ruben C Hartkoorn; Rémi Desmet; Jean-Christophe M Monbaliu; Oleg Melnyk
Journal:  Nat Commun       Date:  2018-07-20       Impact factor: 14.919

Review 8.  Flow Chemistry in Contemporary Chemical Sciences: A Real Variety of Its Applications.

Authors:  Marek Trojanowicz
Journal:  Molecules       Date:  2020-03-21       Impact factor: 4.411

9.  Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis.

Authors:  Sándor B Ötvös; Miquel A Pericàs; C Oliver Kappe
Journal:  Chem Sci       Date:  2019-10-18       Impact factor: 9.825

10.  Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut.

Authors:  Sándor B Ötvös; Patricia Llanes; Miquel A Pericàs; C Oliver Kappe
Journal:  Org Lett       Date:  2020-10-07       Impact factor: 6.005

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