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Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832
[Image: see text] A concise and practical synthesis has been developed to provide the 8-fluoro-5-hydroxy-3,4-diydrocarbostyril (8-FDC) fragment of OPC-167832 in 41% yield and in >99% purity over four steps from 3-amino-4-fluorophenol. The key feature of this process is the development of a telesc...
| Autores principales: | , , , , , , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2022
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8892917/ https://www.ncbi.nlm.nih.gov/pubmed/35252712 http://dx.doi.org/10.1021/acsomega.1c06996 |
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| author | Gopalsamuthiram, Vijayagopal Ho, Dang Binh Peck, Cheryl L. Natarajan, Vasudevan Agrawal, Toolika Burns, Justina M. Bachert, John Cook, Daniel W. Stringham, Rodger W. Nelson, Ryan Ahmad, Saeed Gupton, B. Frank Snead, David R. McQuade, D. Tyler Vaidyanathan, Rajappa Donsbach, Kai Sieber, Joshua D. |
| author_facet | Gopalsamuthiram, Vijayagopal Ho, Dang Binh Peck, Cheryl L. Natarajan, Vasudevan Agrawal, Toolika Burns, Justina M. Bachert, John Cook, Daniel W. Stringham, Rodger W. Nelson, Ryan Ahmad, Saeed Gupton, B. Frank Snead, David R. McQuade, D. Tyler Vaidyanathan, Rajappa Donsbach, Kai Sieber, Joshua D. |
| author_sort | Gopalsamuthiram, Vijayagopal |
| collection | PubMed |
| description | [Image: see text] A concise and practical synthesis has been developed to provide the 8-fluoro-5-hydroxy-3,4-diydrocarbostyril (8-FDC) fragment of OPC-167832 in 41% yield and in >99% purity over four steps from 3-amino-4-fluorophenol. The key feature of this process is the development of a telescoped one-pot synthesis of the quinolone via a chemoselective amidation/acid-induced cyclization that allows for simple product isolation without the need for column chromatography. |
| format | Online Article Text |
| id | pubmed-8892917 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-88929172022-03-03 Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832 Gopalsamuthiram, Vijayagopal Ho, Dang Binh Peck, Cheryl L. Natarajan, Vasudevan Agrawal, Toolika Burns, Justina M. Bachert, John Cook, Daniel W. Stringham, Rodger W. Nelson, Ryan Ahmad, Saeed Gupton, B. Frank Snead, David R. McQuade, D. Tyler Vaidyanathan, Rajappa Donsbach, Kai Sieber, Joshua D. ACS Omega [Image: see text] A concise and practical synthesis has been developed to provide the 8-fluoro-5-hydroxy-3,4-diydrocarbostyril (8-FDC) fragment of OPC-167832 in 41% yield and in >99% purity over four steps from 3-amino-4-fluorophenol. The key feature of this process is the development of a telescoped one-pot synthesis of the quinolone via a chemoselective amidation/acid-induced cyclization that allows for simple product isolation without the need for column chromatography. American Chemical Society 2022-02-18 /pmc/articles/PMC8892917/ /pubmed/35252712 http://dx.doi.org/10.1021/acsomega.1c06996 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Gopalsamuthiram, Vijayagopal Ho, Dang Binh Peck, Cheryl L. Natarajan, Vasudevan Agrawal, Toolika Burns, Justina M. Bachert, John Cook, Daniel W. Stringham, Rodger W. Nelson, Ryan Ahmad, Saeed Gupton, B. Frank Snead, David R. McQuade, D. Tyler Vaidyanathan, Rajappa Donsbach, Kai Sieber, Joshua D. Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832 |
| title | Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832 |
| title_full | Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832 |
| title_fullStr | Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832 |
| title_full_unstemmed | Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832 |
| title_short | Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832 |
| title_sort | development of a practical synthesis of the 8-fdc fragment of opc-167832 |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8892917/ https://www.ncbi.nlm.nih.gov/pubmed/35252712 http://dx.doi.org/10.1021/acsomega.1c06996 |
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