Process Development on an Efficient New Convergent Formal Synthesis of MIV-150

Starting from a known linear route and a proposed convergent route, we have successfully developed a new hybrid convergent route to MIV-150 that takes advantage of the robust chemistry for the preparation of a fluoroketal and the stereospecific Negishi coupling of an iodocyclopropane moiety to a ben...

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Veröffentlicht in:Organic process research & development 2004-05, Vol.8 (3), p.353-359
Hauptverfasser: Cai, Shaopei, Dimitroff, Martin, McKennon, Tracey, Reider, Malcolm, Robarge, Lonnie, Ryckman, David, Shang, Xiao, Therrien, Joseph
Format: Artikel
Sprache:eng
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Zusammenfassung:Starting from a known linear route and a proposed convergent route, we have successfully developed a new hybrid convergent route to MIV-150 that takes advantage of the robust chemistry for the preparation of a fluoroketal and the stereospecific Negishi coupling of an iodocyclopropane moiety to a benzene ring. Stereoselective β- and cis-iodination chemistry was developed for the preparation of an enantiomerically pure iodocyclopropanecarboxylate. Following the Negishi coupling, proven chemistry from the linear route was incorporated, thus ensuring a similar high-purity profile for the final active pharmaceutical ingredient (API). In addition, we have prepared and evaluated a series of basic inorganic and organic MIV-150 salts that have drastically increased water solubility over the parent compound.
ISSN:1083-6160
1520-586X
DOI:10.1021/op0341871