C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 13/04 (2006.01) C07C 1/30 (2006.01) C07C 17/093 (2006.01) C07C 22/00 (2006.01) C07C 51/353 (2006.01) C07C 51/38 (2006.01)
Patent
CA 2298626
The present invention relates generally to novel methods for the synthesis of cyclopropylacetylene which is an essential reagent in the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one; a useful human immunodeficiency virus (HIV) reverse transcriptase inhibitor. In the process, cyclopropane carboxaldehyde is condensed with malonic acid to form 3-cyclopropylacrylic acid; 3- cyclopropylacrylic acid is halogenated to form (E, Z)-1-halo-2- cyclopropylethylene; and (E, Z)-1-halo-2-cyclopropylethylene is dehydrohalogenated to form cyclopropyl acetylene. This improvement provides for high conversion of inexpensive, readily available staring materials into cyclopropylacetylene, high overall yields and can be conducted on an industrial scale.
L'invention porte de manière générale sur des procédés de synthèse du cyclopropylacétylène. Ce réactif est essentiel dans la synthèse asymétrique de la (S)-6-chloro-4-cyclopropyléthynyl-4-trifluorométhyl-1,4-dihydro-2H-3,1-benzoxazin-2-one, un inhibiteur utile de la transciptase inverse du virus de l'immunodéficience humaine (VIH). Dans ce procédé, on condense le cyclopropane carboxaldéhyde avec de l'acide malonique pour former de l'acide 3-cyclopropylacrylique; on halogène cet acide 3-cyclopropylacrylique pour former du (E,Z)-1-halo-2-cyclopropyléthylène; et on déshydrohalogène le (E,Z)-1-halo-2-cyclopropyléthylène pour produire du cyclopropylacétylène. Ce procédé amélioré permet une conversion importante en cyclopropylacétylène de matières premières bon marché et faciles à obtenir. Ce procédé donne un rendement global élevé et convient à l'application à échelle industrielle.
Fortunak Joseph M.
Wang Zhe
Yin Jianguo
Dimock Stratton Llp
Dupont Pharmaceuticals Company
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