SYNTHESIS OF -YL)THIOBUTHYL]-1,2,3-TRIAZOLE-4-YL]METHYLENEPENAM AS BETA-LACTAMASE INHIBITORS

Authors
IM C YIM CB OH JS YOON SB
Citation
C. Im et al., SYNTHESIS OF -YL)THIOBUTHYL]-1,2,3-TRIAZOLE-4-YL]METHYLENEPENAM AS BETA-LACTAMASE INHIBITORS, Archives of pharmacal research, 20(6), 1997, pp. 647-651
Citations number
14
Journal title
Archives of pharmacal research → ACNP
ISSN journal
02536269
Volume
20
Issue
6
Year of publication
1997
Pages
647 - 651
Database
ISI
SICI code
0253-6269(1997)20:6<647:SO-AB>2.0.ZU;2-Z
Abstract
The 6,6-dibromopenam 6 was treated with CH3MgBr and carbaldehyde 5 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 7, which was re acted with acetic anhydride to give acetoxy compound 8. The deacetobro mination of 8 with zinc and acetic acid gave 6-exomethylenpenams, Z-is omer 9 and E-isomer 10, which were oxidized to sulfones 11 and 12 by m -CPBA. The p-methoxybenzyl compounds were deprotected by AlCl3 and neu tralized to give the sodium salts 13, 14, and 15.