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    • 4. 发明授权
    • Process for the preparation of 4-substituted azetidinone derivatives
    • 制备4-取代的氮杂环丁酮衍生物的方法
    • US06340751B1
    • 2002-01-22
    • US09357153
    • 1999-07-19
    • Takao SaitoToshiyuki MurayamaTakaji MatsumotoTakashi Miura
    • Takao SaitoToshiyuki MurayamaTakaji MatsumotoTakashi Miura
    • C07F718
    • C07D413/06C07D205/08Y02P20/55
    • Disclosed is a process for the preparation of a 4-substituted azetidinone derivative, which comprises reacting an azetidinone derivative and an amide compound in the presence of a magnesium compound such as those represented by the following formulas (II): and (IV): represented by the following formula (III): MgR5R6  (III) wherein R5 represents a C1-12 alkyl group, a C2-5 alkenyl group, a 5- to 8-membered alicyclic group which may be substituted by a lower C1-4 alkyl group, a phenyl group which may be substituted by a lower C1-4 alkyl group, a lower C1-4 alkoxy group or a halogen atom or a benzyl group which may be substituted by a lower C1-4 alkyl group, a lower C1-4 alkoxy group or a halogen atom, and R6 represents a halogen atom, a methanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, an acetoxy group which may be substituted by a halogen atom or a cyano group or an OR7 group (R7 representing a lower C1-4 alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group). The process provides an industrially excellent process for the preparation of a 4-substituted azetidinone derivative which permits the selective preparation of an intermediate for the synthesis of a carbapenem antibacterial agent having a desired 1-&bgr;′ configuration.
    • 公开了制备4-取代的氮杂环丁酮衍生物的方法,该方法包括在镁化合物如下式(II)和(IV)所示的那些镁化合物存在下使氮杂环丁酮衍生物与酰胺化合物反应:代表 通过下式(III)表示:其中R5表示C1-12烷基,C2-5烯基,可被低级C1-4烷基取代的5至8元脂环基,苯基 可以被低级C 1-4烷基,低级C 1-4烷氧基或卤素原子取代的苯基,或可以被低级C 1-4烷基取代的苄基,低级C 1-4烷氧基或 卤原子,R6表示卤原子,甲磺酰氧基,苯磺酰氧基,对甲苯磺酰氧基,三氟甲磺酰氧基,可被卤素原子或氰基取代的乙酰氧基或OR7基(R7表示 低级C 1-4烷基,取代的o R未取代的苯基或取代或未取代的苄基)。 该方法提供了制备4-取代的氮杂环丁酮衍生物的工业上优异的方法,其允许选择性制备用于合成具有所需1-β'构型的碳青霉烯类抗菌剂的中间体。
    • 7. 发明授权
    • Process for producing optically active &ggr;-butyrolactone
    • 光学活性γ-丁内酯的制备方法
    • US06608214B2
    • 2003-08-19
    • US10199136
    • 2002-07-19
    • Tsukasa SotoguchiTakaji MatsumotoMotonobu TakenakaTakashi Miura
    • Tsukasa SotoguchiTakaji MatsumotoMotonobu TakenakaTakashi Miura
    • C07D30733
    • C07D307/33C07B2200/07C07C67/31Y02P20/55C07C69/734
    • This invention provides a novel process for producing optically active 3-hydroxy-&ggr;-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-&ggr;-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.
    • 本发明提供了一种在短时间内制备光学活性3-羟基-γ-丁内酯的新方法,其经济性和效率都优异,在工业上适用于便宜且易于获得的试剂和易于处理的试剂。 本发明涉及一种由式I表示的光学活性3-羟基-γ-丁内酯的制备方法:其中符号*表示不对称碳原子,其包括将由式II表示的光学活性的4-取代的氧基-3-羟基丁酸 :其中R1表示C1-4低级烷基,R2表示通过异相氢化催化剂氢化脱保护的羟基的保护基,符号*具有与上述相同的含义,在非均相加氢催化剂存在下 和酸性物质,然后脱保护并同时闭环。