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



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 


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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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