Invention Grant
US5712388A Method of preparing a derivative of optically active azetidin-2-one
失效
制备光学活性氮杂环丁烷-2-酮衍生物的方法
- Patent Title: Method of preparing a derivative of optically active azetidin-2-one
- Patent Title (中): 制备光学活性氮杂环丁烷-2-酮衍生物的方法
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Application No.: US648516Application Date: 1996-05-13
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Publication No.: US5712388APublication Date: 1998-01-27
- Inventor: Takaji Matsumoto , Toshiyuki Murayama , Takashi Miura
- Applicant: Takaji Matsumoto , Toshiyuki Murayama , Takashi Miura
- Applicant Address: JPX Tokyo
- Assignee: Takasago International Corporation
- Current Assignee: Takasago International Corporation
- Current Assignee Address: JPX Tokyo
- Priority: JPX7-135614 19950511
- Main IPC: C07D205/08
- IPC: C07D205/08 ; C07C229/22 ; C07F7/18
Abstract:
To prepare the compound (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one, (2S,3R)-2-aminomethyl-3-hydroxybutyric acid is reacted with an alcohol in the presence of at least one compound chosen from the group consisting of thionyl chloride, hydrogen chloride and p-toluene sulfonic acid, thereby obtaining a salt of the corresponding ester. The salt is reacted with a tri-substituted silane in the presence of a metallic catalyst, thereby protecting the hydroxy group of the ester and then reacted with a base, thereby obtaining an ester of (2S,3R)-2-aminomethyl-3-(tri-substituted silyloxy)butyric acid. Subsequently, the ester is transformed into lactam in the presence of a Grignard reagent or a metal amide, thereby obtaining (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one. This compound provides a useful base for preparing .beta.-lactam type antimicrobial agents such as carbapenem type agents.
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