A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow
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 overa...
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| Format: | Article |
| Language: | en_US |
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Wiley Blackwell
2018
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| Online Access: | http://hdl.handle.net/1721.1/114538 https://orcid.org/0000-0001-7266-9350 https://orcid.org/0000-0001-5511-5620 https://orcid.org/0000-0002-8601-7799 https://orcid.org/0000-0001-7192-580X |
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| author | Lin, Hongkun Dai, Chunhui Jamison, Timothy F Jensen, Klavs F |
| author2 | Massachusetts Institute of Technology. Department of Chemical Engineering |
| author_facet | Massachusetts Institute of Technology. Department of Chemical Engineering Lin, Hongkun Dai, Chunhui Jamison, Timothy F Jensen, Klavs F |
| author_sort | Lin, Hongkun |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T12:50:03Z |
| format | Article |
| id | mit-1721.1/114538 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T12:50:03Z |
| publishDate | 2018 |
| publisher | Wiley Blackwell |
| record_format | dspace |
| spelling | mit-1721.1/1145382022-09-28T10:20:03Z A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow Lin, Hongkun Dai, Chunhui Jamison, Timothy F Jensen, Klavs F Massachusetts Institute of Technology. Department of Chemical Engineering Massachusetts Institute of Technology. Department of Chemistry Jamison, Timothy F. Lin, Hongkun Dai, Chunhui Jamison, Timothy F Jensen, Klavs F 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. United States. Defense Advanced Research Projects Agency (Grant N666001-11-C-4005) 2018-04-04T15:40:58Z 2018-04-04T15:40:58Z 2017-07 2017-04 Article http://purl.org/eprint/type/JournalArticle 1433-7851 1521-3773 http://hdl.handle.net/1721.1/114538 Lin, Hongkun et al. “A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow.” Angewandte Chemie International Edition 56, 30 (June 2017): 8870–8873 © 2017 Wiley‐VCH Verlag GmbH & Co https://orcid.org/0000-0001-7266-9350 https://orcid.org/0000-0001-5511-5620 https://orcid.org/0000-0002-8601-7799 https://orcid.org/0000-0001-7192-580X en_US http://dx.doi.org/10.1002/anie.201703812 Angewandte Chemie International Edition Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ application/pdf Wiley Blackwell Prof. Jensen via Erja Kajosalo |
| spellingShingle | Lin, Hongkun Dai, Chunhui Jamison, Timothy F Jensen, Klavs F A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow |
| title | A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow |
| title_full | A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow |
| title_fullStr | A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow |
| title_full_unstemmed | A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow |
| title_short | A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow |
| title_sort | rapid total synthesis of ciprofloxacin hydrochloride in continuous flow |
| url | http://hdl.handle.net/1721.1/114538 https://orcid.org/0000-0001-7266-9350 https://orcid.org/0000-0001-5511-5620 https://orcid.org/0000-0002-8601-7799 https://orcid.org/0000-0001-7192-580X |
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