Tanomastat, BAY-12-9566
(S)-4-(4’-氯联苯-4-基)-4-氧代-2-(苯硫基甲基)丁酸Chemical Name: 4-(4'-Chlorobiphenyl-4-yl)-4-oxo-2(S)-(phenylsulfanylmethyl)butyric acid
CAS No. 179545-77-8, 215258-80-3 (error), 179545-78-9 (R-isomer), 179545-76-7 (undefined isomer)
项目整合开发状态: Phase III
项目研究机构: Bayer (Originator)
合成路线:The Friedel-Crafts condensation of 4-chlorobiphenyl (I) with 3-methylenetetrahydrofuran-2,5-dione (II) by means of AlCl3 in tetrachloroethane gives 4-(4'-chlorobiphenyl-4-yl)-2-methylene-4-oxobutyric acid (III),which is treated with thiophenol (IV) and K2CO3 in DMF/water,yielding racemic 4-(4'-chlorobiphenyl-4-yl)-4-oxo-2-(phenylsulfanylmethyl)butyric acid (V).Finally,racemic (V) is resolved by means of crystallization with (+)-cinchonine in acetone.
📌 参考资料/链接：
参考文献标题:Substd.4-biarylbutyric or 5-biarylpentanoic acids and derivs.as matrix metalloprotease inhibitors
文献作者:Kluender,H.C.E.; Benz,G.H.H.H.; Brittelli,D.R.; Bullock,W.H.; Combs,K.J.; Dixon,B.R.; Schneider,S.; Wood,J.E.; Vanzandt,M.C.; Wolanin,D.J.; Wilhelm,S.M.(Bayer AG)
参考来源:EP 0790974; JP 1998509146; US 5789434; US 5859047; WO 9615096
📄 详细内容
合成路线:The Friedel-Crafts condensation of 4-chlorobiphenyl (I) with 3-methylenetetrahydrofuran-2,5-dione (II) by means of AlCl3 in tetrachloroethane gives 4-(4'-chlorobiphenyl-4-yl)-2-methylene-4-oxobutyric acid (III),which is treated with thiophenol (IV) and K2CO3 in DMF/water,yielding racemic 4-(4'-chlorobiphenyl-4-yl)-4-oxo-2-(phenylsulfanylmethyl)butyric acid (V).Finally,racemic (V) is resolved by means of crystallization with (+)-cinchonine in acetone.
参考文献标题:Bay-12-9566
文献作者:Sorbera,L.A.; Castar,J.; Graul,A.; Silvestre,J.S.
参考来源:Drugs Fut 1999,24(1),16
产品链接: CAS No. 179545-77-8›› 产品链接: CAS No.179545-78-9››