(Z)-2-(5-氨基-1,2,4-噻二唑-3-基)-2-甲氧亚氨基乙酸的合成

Synthesis of a cefozopran intermediate(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetic acid

目的合成头孢唑兰中间体(Z)-2-(5-氨基-1,2,4-噻二唑-3-基)-2-甲氧亚氨基乙酸。方法以氰乙酰胺为起始原料,依次经甲氧亚氨化、加成、酯化、与硫氰化钾反应、构型转换和水解共6步反应制得目标化合物。结果与结论目标化合物的结构经1H-NMR和MS谱确证。该工艺路线原料易得,操作简便,总收率为29.8%,具有一定的工业化价值。

Aim To synthesize （Z） -2- （ 5-amino-1,2,4-thiadiazol-3-yl） -2-methoxyiminoacetic acid, a key intermediate of cefozopran. Methods The target compound was synthesized from 2-cyanoacetamide via methoxyimination, addition, esterification, reaction with potassium thiocyanate, configuration transformation and then hydrolysis. Results and conclusion The target compound was synthesized with an overall yield of 29.8 %, and its structure was identified by ^1H-NMR and MS. This procedure can be used in the industrial manufacture due to its advantages of cheap starting material and convenient operation.