Development of a Practical Synthesis of the 8‑FDC Fragment of OPC-167832

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 synth...

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Published inACS omega Vol. 7; no. 8; pp. 7223 - 7228
Main Authors 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
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.03.2022
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Summary: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.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.1c06996