Development of an Alternative Process for the Manufacture of a Key Starting Material for Cefovecin Sodium

A process has been developed for the use of trimethylphosphite for the formation of the six-membered 3,6-dihydro-2H-[1,3]thiazine ring in the cephem architecture by an intramolecular Horner−Emmons−Wadsworth condensation. The process is a suitable alternative to the traditional Wittig process, which...

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Bibliographic Details
Published inOrganic process research & development Vol. 11; no. 4; pp. 742 - 746
Main Authors Norris, Timothy, Nagakura, Isao, Morita, Hiromasa, McLachlan, Grant, Desneves, Joe
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.07.2007
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Summary:A process has been developed for the use of trimethylphosphite for the formation of the six-membered 3,6-dihydro-2H-[1,3]thiazine ring in the cephem architecture by an intramolecular Horner−Emmons−Wadsworth condensation. The process is a suitable alternative to the traditional Wittig process, which uses trimethylphosphine. The process developed is a highly telescoped reaction pathway consisting of at least six known reaction intermediates that was scaled for production use to produce 2.
ISSN:1083-6160
1520-586X
DOI:10.1021/op700091d