合成路线:The reaction of 2-(2-sulfanylthiazol-4-yl)acetic acid ethyl ester (I) with ammonia and ammonium chloride gives the corresponding acetamide (II),which is condensed with the cephem methanesulfonate (III) by means of potassium tert-butoxide in dimethoxyethane to yield the diphenylmethyl ester (IV) of the target compound,which is finally hydrolyzed with trifluoroacetic acid and anisole.
合成路线:In an alternative method,benzhydryl ester (V) was cleaved with trifluoroacetic acid to give carboxylic acid (VI).After protection of (VI) by means of trimethylsilyl acetamide,the triflate group was displaced by the potassium salt of mercapto thiadiazole (III) to furnish the title compound.
参考文献标题:New cephem cpds.and pharmaceutical use thereof
文献作者:Yoshida,Y.; Okuda,S.; Sasaki,H.; Matsuda,K.; Takasugi,H.(Fujisawa Pharmaceutical Co.,Ltd.)
参考来源:EP 0882052; JP 2000505432; WO 9729111
合成路线:The title compound has been prepared by two related procedures: Treatment of 3-hydroxy cephem derivative (I) with methanesulfonyl chloride and K2CO3 afforded mesylate (II),which was condensed with 2-mercapto-5-methyl-1,3,4-thiadiazole (III) in the presence of potassium tert-butoxide to give thioether (IV).The benzhydryl ester of (IV) was then deprotected by treatment with trifluoroacetic acid.
参考文献标题:Synthesis and anti-Helicobacter pylori activity of FR182024,a new cephem derivative
文献作者:Yoshida,Y.; Matsuda,K.; Sasaki,H.; Matsumoto,Y.; Matsumoto,S.; Takasugi,H.
参考来源:Bioorg Med Chem Lett 1999,9(21),3123
合成路线:The title compound has been prepared by two related procedures: Treatment of 3-hydroxy cephem derivative (I) with methanesulfonyl chloride and K2CO3 afforded mesylate (II),which was condensed with 2-mercapto-5-methyl-1,3,4-thiadiazole (III) in the presence of potassium tert-butoxide to give thioether (IV).The benzhydryl ester of (IV) was then deprotected by treatment with trifluoroacetic acid.
合成路线:In an alternative method,benzhydryl ester (V) was cleaved with trifluoroacetic acid to give carboxylic acid (VI).After protection of (VI) by means of trimethylsilyl acetamide,the triflate group was displaced by the potassium salt of mercapto thiadiazole (III) to furnish the title compound.
参考文献标题:Studies of anti-Helicobacter pylori agents.Part 2: New cephem derivatives
文献作者:Yoshida,Y.; Matsuda,K.; Sasaki,H.; Matsumoto,Y.; Matsumoto,S.; Tawara,S.; Takasugi,H.
参考来源:Bioorg Med Chem 2000,8(9),2317
产品链接: CAS No. 179034-83-4››