Archives of Pharmacal Research
- Volume 22 Issue 1
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- Pages.68-71
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- 1999
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- 0253-6269(pISSN)
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- 1976-3786(eISSN)
Synthesis of 6-Exomethylenepenams as $\beta-Lactamase$ Inhibitors
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Im, Cha-Euk
(College of Pharmacy, Chung-Ang University) ;
- Oh, Jung-Suk (College of Pharmacy, Chung-Ang University) ;
- Yim, Chul-Bu (College of Pharmacy, Chung-Ang University)
- Published : 1999.02.01
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.