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项目整合精选>>>Tazobactam sodium, YP-14(comb. with piperacillin), CL-307579, CL-298741(free acid), YTR-830H, YTR-830(free acid), Tazocilline(comb. with piperacillin), Tazocin(comb. with piperacillin), Tazobac, Astat
Tazobactam sodium, YP-14(comb. with piperacillin), CL-307579, CL-298741(free acid), YTR-830H, YTR-830(free acid), Tazocilline(comb. with piperacillin), Tazocin(comb. with piperacillin), Tazobac, Astat
他唑巴坦钠 三唑巴坦 Chemical Name: [2S-(2alpha,3beta,5alpha)]-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide sodium salt
CAS No. 89785-84-2, 89786-04-9 (free acid)
项目整合开发状态: Launched-1992
项目研究机构: Taiho (Originator), Toyama (Licensee), Wyeth Pharmaceuticals (Licensee)
合成路线:1) The reaction of benzhydryl 2alpha-methyl-2beta-(chloromethyl)penam-3alpha-carboxylate (I) with sodium azide in DMF gives the corresponding azidomethyl derivative (II),which is oxidized with KMnO4 in aqueous acetic acid to the dioxide (III).The cyclization of (III) with trimethylsilylacetylene (IV) at 95 C yields benzhydryl 2a-methyl-2B-(4 trimethylsilyl-1,2,3-triazol-1 ylmethyl)penam 3a-carboxylate-1,1-dioxide (V),which is desilylated with KF and 18-crown-6 in hot DMF affording the benzhydryl ester of YTR-830 (VI).Then this compound is submitted to hydrogenolysis with H2 over Pd/C in ethyl / acetate / water.
合成路线:2) The ester (VI) can also be obtained by cyclization of (III) with vinyl acetate (VII) at 110 C.
📌 参考资料/链接：
参考文献标题:Penicillin derivatives and process for preparation of the same
文献作者:Micetich,R.G.; et al.(Taiho Pharmaceutical Co.,Ltd.)
参考来源:EP 0097446; ES 523701; ES 538020
📄 详细内容
合成路线:1) The reaction of benzhydryl 2alpha-methyl-2beta-(chloromethyl)penam-3alpha-carboxylate (I) with sodium azide in DMF gives the corresponding azidomethyl derivative (II),which is oxidized with KMnO4 in aqueous acetic acid to the dioxide (III).The cyclization of (III) with trimethylsilylacetylene (IV) at 95 C yields benzhydryl 2a-methyl-2B-(4 trimethylsilyl-1,2,3-triazol-1 ylmethyl)penam 3a-carboxylate-1,1-dioxide (V),which is desilylated with KF and 18-crown-6 in hot DMF affording the benzhydryl ester of YTR-830 (VI).Then this compound is submitted to hydrogenolysis with H2 over Pd/C in ethyl / acetate / water.
合成路线:2) The ester (VI) can also be obtained by cyclization of (III) with vinyl acetate (VII) at 110 C.
合成路线:The title amide is obtained by condensation of 6-methylpyridine-3-carboxylic acid (I) with 4-ethoxy-2-nitroaniline by means of cyanuric chloride and TEA in dichloromethane.
参考文献标题:Substd.nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof
文献作者:Cai,S.X.; Drewe,J.A.(Cytovia,Inc.)
参考来源:WO 0155115
产品链接: CAS No. 89785-84-2›› 产品链接: CAS No.89786-04-9››