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...

Descripción completa

Detalles Bibliográficos
Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
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
Descripción
Sumario:[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.

Ejemplares similares