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KMID : 0043319970200060647
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Archives of Pharmacal Research
1997 Volume.20 No. 6 p.647 ~ p.651
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Synthesis of 6-[1-[4-(Benzoxazol-2-yl)thiobuthyl]-1,2,3-triazole-4-yl]methylenepenam as β-Lactamase Inhibitors
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Im Chae-Uk
Yim Chul-Bu
Oh Jung-Suk
Yoon Sang-Bae
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Abstract
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The 6, 6-dibromopenam 6 was treated with and carbaldehyde 5 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 7, which was reacted with acetic anhybride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 9 and E-isomer 10, which were oxidized to sulfones 11 and 12 by m-CPBA. The p-methoxybenzyl compounds were deprotected by and neutralized to give the sodium salts 13, 14, and 15.
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KEYWORD
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Triazole, 6-Exomethylenepenam, b-Lactamase inhibitors
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