Английская Википедия:Cefroxadine
Шаблон:Short description Шаблон:Drugbox 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.[1]
It is available in Italy.[2]
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).
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).
See also
References
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite patent
- ↑ R. Scartazzini, H. Bickel, Шаблон:US patent (1978 to Ciba-Geigy).
- ↑ R. B. Woodward and H. Bickel, Шаблон:US Patent (1979); Chem. Abstr., 91, 74633J (1979).
Шаблон:CephalosporinAntiBiotics
