Research on Chemical Intermediates

, Volume 40, Issue 5, pp 2139–2143 | Cite as

The synthesis of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid

  • Yougui Zhao
  • Ronggeng Wang
  • Mei Liu


The objective was to synthesize (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid (the side chain for Ceftaroline fosamil). Oximation and alkylation were used on cyanoacetamide to get 2-cyano-2-hydroxyiminoacetamide, which became 2-ethyoxyiminopropanedinitrile through reaction with phosphorus oxychloride, and then aminolysis to get 2-ethoxyiminopropanedinitrile, which became 2-ethoxyimion-2-(5-amino-1,2,4 thiadiazol-3-yl) acetonitrile by brominating and with KSCN, followed by hydrolysis to get (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid.


Ceftaroline fosamil Oximation Alkylation Aminolysis Brominating Cyclization 1,2,4 thiadiazol 


  1. 1.
    Meng Xian-min, Yao Xiao-ying et al., Ceftaroline, a new cephalosporin. Chi. J. Antibiot. [J]. 35(1), 7–12, 19 (2010)Google Scholar
  2. 2.
    Tsutomu Teraji, Kazuo Sakane, Jiro Goto. Processes for preparing 2-substituted hydroxyimino-2-(5-amino-1,2,4-thiadiazol-3yl)acetic acid or its salt, and intermediates thereof. GB 2094794 [P]. 1982-03-01Google Scholar
  3. 3.
    Yi Hhengping, Li Jing et al., The preparation of 2-oxime-2-(-1,2,4-tetrazolium-3-) acetic acid compounds. CN 101987837 [P]. 2010-01-12Google Scholar
  4. 4.
    Yoshitaka, Shundo, Takuji, Fujii, Toshihide. Preparation of thiadiazoleacetate crystals as materials for cephalosporins. JP 04077477 [P].1992-03-11Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  1. 1.Hebei chem&pharm cocational technology collageShijiazhuang, HebeiChina
  2. 2.Hebei University of Science and TechnologyShijiazhuangChina
  3. 3.Hebei Medical UniversityShijiazhuang, HebeiChina

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