Possibilities to acylate 7-aminocephalosporanic acid to obtain some cephalosporins

Rev Med Chir Soc Med Nat Iasi. 2014 Jan-Mar;118(1):244-9.

Abstract

Aim: Acylation of 7-aminocephalosporanic acid with an adequate acyl chloride in order to obtain cefotaxime sodium salt.

Material and methods: Cefotaxime sodium salt was synthesized by acylating 7-amino cephalosporanic acid with 2-[2'-chloracetamidothiazole-4-yl]-2-(syn)-methoxy-imino acetic chloride in four steps. The melting point was determined, and IR spectral analysis and elemental analysis were performed to confirm cefotaxime structure. The quantitative determination was performed.

Results: The reaction conditions were established. The yield of the synthesis phases (73-80%) and actual yield (45-47%) were very good. The structure of the obtained cefotaxime sodium salt was confirmed by the IR spectral analysis and by elemental analysis (C, H, N). The melting point was 163 degrees C. The purity of the synthesized cefotaxime sodium salt was 98.9%.

Conclusions: Cefotaxime sodium salt was synthesized by acylation of 7-aminocephalosporanic acid with 2-[2'-chloracetamidothiazole-4-yl]-2-(syn)-methoxy-imino acetic chloride, in aqueous solution, then transformed into sodium salt with sodium 2-ethylhexanoate. The method proved to be very good, yields were good, it is reproducible and simple, and does not involve high risks, so it is also safe.

MeSH terms

  • Acetates
  • Acylation
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Cefotaxime / chemical synthesis*
  • Cefotaxime / pharmacology
  • Cephalosporins / chemical synthesis
  • Cephalosporins / chemistry*
  • Indicators and Reagents
  • Reproducibility of Results
  • Spectrophotometry, Infrared
  • Water / chemistry

Substances

  • Acetates
  • Anti-Bacterial Agents
  • Cephalosporins
  • Indicators and Reagents
  • Water
  • 7-aminocephalosporanic acid
  • Cefotaxime