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

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Abstract

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.

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References

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Authors and Affiliations

  1. Hebei chem&pharm cocational technology collage, Shijiazhuang, Hebei, China

    Yougui Zhao

  2. Hebei University of Science and Technology, Shijiazhuang, China

    Ronggeng Wang

  3. Hebei Medical University, Shijiazhuang, Hebei, China

    Mei Liu

Authors
  1. Yougui Zhao
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  2. Ronggeng Wang
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  3. Mei Liu
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Correspondence to Ronggeng Wang.

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Zhao, Y., Wang, R. & Liu, M. The synthesis of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid. Res Chem Intermed 40, 2139–2143 (2014). https://doi.org/10.1007/s11164-013-1109-0

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  • DOI: https://doi.org/10.1007/s11164-013-1109-0

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