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Cefroxadine

Chemical compound

Cefroxadine
Summary

Chemical compound

| Drugs.com =

| elimination_half-life = ~1 hour

Cefroxadine (INN, trade names Oraspor and Cefthan-DS) is a cephalosporin antibiotic. It is structurally related to cefalexin, and both drugs share a similar spectrum of activity.

It is available in Italy.

Synthesis

Cefroxadine can be prepared by several routes, including one in which the enol is methylated with diazomethane as a key step. A rather more involved route starts with comparatively readily available phenoxymethylpenicillin sulfoxide benzhydryl ester (1).

4147864}} (1979); Chem. Abstr., 91, 74633J (1979).</ref>]]{{clear left}}

This undergoes fragmentation when treated with benzothiazole-2-thiol to give 2. Ozonolysis (reductive work-up) cleaves the olefinic linkage and the unsymmetrical disulfide moiety is converted to a tosyl thioester (3). The enol moiety is methylated with diazomethane, the six-membered ring is closed by reaction with 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU), and the ester protection is removed with trifluoroacetic acid to give 4. The amide side chain is removed by the usual PCl5/dimethylaniline sequence followed by reamidation with the appropriate acid chloride to give cefroxadine (5).

References

References

  1. (July 1980). "Cefroxadine (CGP-9000), an orally active cephalosporin". [[Antimicrobial Agents and Chemotherapy]].
  2. [No authors listed]. "Oraspor". Elsevier.
  3. "Enolderivate [Enol derivatives]".
  4. R. Scartazzini, H. Bickel, {{US patent. 4073902 (1978 to Ciba-Geigy).
  5. R. B. Woodward and H. Bickel, {{US Patent. 4147864 (1979); Chem. Abstr., 91, 74633J (1979).
Wikipedia Source

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cephalosporin-antibiotics enantiopure-drugs enol-ethers
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