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Synthesis of 6-exomethylenepenams as beta-lactamase inhibitors

Authors
Im, COh, JSYim, CB
Issue Date
Feb-1999
Publisher
PHARMACEUTICAL SOCIETY KOREA
Keywords
triazole; 6-exomethylenepenam; beta-lactamase inhibitors
Citation
ARCHIVES OF PHARMACAL RESEARCH, v.22, no.1, pp 68 - 71
Pages
4
Journal Title
ARCHIVES OF PHARMACAL RESEARCH
Volume
22
Number
1
Start Page
68
End Page
71
URI
https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/25430
DOI
10.1007/BF02976438
ISSN
0253-6269
Abstract
The 6,6-dibromopenam (6) was treated with CH3MgBr and carbaldehyde 5 to afford the hydroxy compound 7, which was reacted with acetic anhydride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenepenams, E-isomer 10 and Z-isomer 9, which was oxidized to sulfone 11 by m-CPBA. The p-methoxybenzyl compounds were deprotected by AlCl3 and neutralized to give the sodium salts 12, 13 and 14.
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약학대학 (약학부)
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