YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis of 6-Exomethylene Sulbactam Derivatives

6-엑소메칠렌 Sulbactam 유도체의 합성

  • 임채욱 (중앙대학교 약학대학 의약화학 교실) ;
  • 정홍식 (중앙대학교 약학대학 의약화학 교실) ;
  • 임철부 (중앙대학교 약학대학 의약화학 교실)
  • Published : 2002.12.01
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Abstract

The synthesis of new 6-exomethylene sulbactam derivatives with 5-methyl-1,3,4-thiadiazole was described. The 6,6-dibromopenam 5 was reacted with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was treated with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylen penams, Z-isomer 8 and E-isomer 9, which was oxidized to sulfones 10 by m-CPBA. The p-methoxybenzyl compounds 6-10 were deprotected by AlCl$_3$ and neutralized with NaOH solution to give the sodium salts 11-15.

Keywords

References

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