发明授权
- 专利标题: Process for the stereospecific synthesis of azetidinones
- 专利标题(中): 立体定向合成氮杂环丁酮的方法
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申请号: US179008申请日: 1994-01-07
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公开(公告)号: US6093812A公开(公告)日: 2000-07-25
- 发明人: Tiruvettipuram K. Thiruvengadam , Chou-Hong Tann , Junning Lee , Timothy McAllister , Cesar Colon , Derek H. R. Barton , Ronald Breslow , Anantha Sudhakar
- 申请人: Tiruvettipuram K. Thiruvengadam , Chou-Hong Tann , Junning Lee , Timothy McAllister , Cesar Colon , Derek H. R. Barton , Ronald Breslow , Anantha Sudhakar
- 申请人地址: NJ Kenilworth
- 专利权人: Schering Corporation
- 当前专利权人: Schering Corporation
- 当前专利权人地址: NJ Kenilworth
- 主分类号: A61K31/395
- IPC分类号: A61K31/395 ; A61K31/397 ; A61K31/40 ; A61K31/415 ; A61K31/44 ; A61K31/4427 ; A61K31/443 ; A61K31/4433 ; A61K31/47 ; A61K31/495 ; A61K31/535 ; A61K31/695 ; A61P3/06 ; A61P9/10 ; C07D205/08 ; C07D205/085 ; C07D401/04 ; C07D403/04 ; C07D405/04 ; C07D405/10 ; C07D409/04 ; C07D413/10 ; C07F7/08 ; C07F7/10 ; C07F7/18
摘要:
This invention provides an improved process for producing azetidinones. More particularly, this invention provides the steps of producing an trans-azetidinone represented by the formula ##STR1## from a carboxylic acid R.sup.2 --D--CH.sub.2 COOH, an aldehyde R.sup.1 --A--CHO and an amine RNH.sub.2, by the steps of: (a1) converting a carboxylic acid to the corresponding acid chloride; (b1) deprotonating a chiral oxazolidinone and treating the resulting anion with the product of step (a1); (c1) enolizing the product of step (b1) and condensing with the aldehyde; (d1) hydrolyzing the product of step (c1); (e1) condensing the product of step (d1) with the amine; and (f1) cyclizing the product of step (e1). Alternatively, the process comprises (a2) enolizing the product of step (b1) and condensing, in the presence of a Lewis acid, with a Schiff's base prepared from the aldehyde and the amine; and (b2) cyclizing the product of step (a2).
公开/授权文献
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