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21. 发明授权

US06313315B1 Methods for producing N-protected-azetidine-2-carboxylic acids 失效
标题翻译： N-保护氮杂环丁烷-2-羧酸的制备方法
公开(公告)号：US06313315B1
公开(公告)日：2001-11-06
申请号：US09584853
申请日：2000-06-01
申请人： Kazuhiro Yamauchi , Hideki Ushio , Isao Kurimoto
发明人： Kazuhiro Yamauchi , Hideki Ushio , Isao Kurimoto
IPC分类号： C07D20504
CPC分类号： C07D205/04
摘要： There is disclosed a method for producing an essentially enantiomerically pure N-protected-azetidine-2-carboxylic acid of formula (1): which method is characterized by: subjecting a crude enantiomerically excess N-protected-azetidine-2-carboxylic acid comprising said enantiomer represented by formula (1) in excess to the other enantiomer thereof to crystallization in an organic solvent selected from aromatic hydrocarbon, aliphatic ether, aliphatic alcohol, aliphatic ketone, aliphatic nitrile, aliphatic amide, aliphatic sulfoxide, aliphatic ester and a mixed solvent thereof, wherein R is: an optionally substituted alkyl, alicyclic or alicyclicalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, or a dialkylamino group, and absolute configuration of the asterisked asymmetric carbon atom is S or R.
摘要翻译：公开了一种制备基本上对映体纯的式（1）的N-保护的氮杂环丁烷-2-羧酸的方法：该方法的特征在于：将粗对映异构体过量的N-保护的氮杂环丁烷-2-羧酸由式（1）表示的对映异构体与其它对映异构体反应，在选自芳族烃，脂族醚，脂族醇，脂族酮，脂族腈，脂族酰胺，脂族亚砜，脂族酯及其混合溶剂的有机溶剂中结晶其中R是：任选取代的烷基，脂环族或脂环族烷基，任选取代的烯基，任选取代的芳基，任选取代的杂芳基或二烷基氨基，并且星号不对称碳原子的绝对构型是S或R.

22. 发明授权

US06277998B1 Production process and intermediate of tetrazole compound 失效
公开(公告)号：US06277998B1
公开(公告)日：2001-08-21
申请号：US09662591
申请日：2000-09-14
申请人： Hideki Ushio , Takayuki Higashii , Masayoshi Minai , Akihiko Nakamura
发明人： Hideki Ushio , Takayuki Higashii , Masayoshi Minai , Akihiko Nakamura
IPC分类号： C07D40504
CPC分类号： C07D257/04 , C07C251/86 , C07C257/18 , C07C257/22 , C07D405/04
摘要： There are disclosed an industrially favorable process for producing a tetrazole compound of general formula (1): characterized in that a nitrile of general formula (2): R1CN (2) is reacted with hydrazine or a salt thereof in the presence of a catalyst, followed by reaction with a nitrous acid compound of general formula (3): ANO2 (3) or a nitrile of general formula (2) is reacted with hydrogen sulfide, followed by reaction with an alkyl halide of general formula (4): R4J (4) with hydrazine or a salt thereof, and then with a nitrous acid compound of general formula (3); and an intermediate of general formula (5): R1C(═R5)R6 (5) which is useful for the production of the tetrazole compound (in which R1 to R6, A and J in the above formulas are as defined in the specification).

23. 发明授权

US5637736A Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof 失效
标题翻译：制备1-溴烷基苯衍生物的方法及其中间体
公开(公告)号：US5637736A
公开(公告)日：1997-06-10
申请号：US286411
申请日：1994-08-05
申请人： Hiroaki Fujishima , Yasunobu Miyamoto , Masayoshi Minai , Tsutomu Matsumoto , Hideki Ushio , Takayuki Higashii
发明人： Hiroaki Fujishima , Yasunobu Miyamoto , Masayoshi Minai , Tsutomu Matsumoto , Hideki Ushio , Takayuki Higashii
IPC分类号： C07C15/44 , C07C17/08 , C07C17/087 , C07C17/26 , C07C41/22 , C07F3/02 , C07D319/14
CPC分类号： C07C17/2632 , C07C15/44 , C07C17/08 , C07C17/087 , C07C41/22 , C07F3/02
摘要： A 1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent. The phenylalkene derivative is prepared by reacting an alkenyl halide with metal magnesium to form a Grignard reagent, and then reacting the Grignard reagent with a benzyl halide derivative. An allyl Grignard reagent is prepared by reacting continuously an allyl halide derivative with metal magnesium in an organic solvent, in which the allyl halide derivative and metal magnesium are continuously added to the reaction system and the allyl Grignard reagent formed is continuously removed from the reaction system. The processes provide the intended compounds in high yields, high selectivities and high purities.
摘要翻译：通过在非极性溶剂存在下使苯基烯烃衍生物与溴化氢反应来制备1-溴烷基苯衍生物。苯基烯烃衍生物通过烯基卤化物与金属镁反应形成格氏试剂制备，然后使格利雅试剂与苄基卤衍生物反应。通过连续将烯丙基卤衍生物与金属镁在有机溶剂中连续反应制备烯丙基格氏试剂，其中将烯丙基卤衍生物和金属镁连续加入到反应体系中，形成的烯丙基格氏试剂从反应体系中连续除去。这些方法以高产率，高选择性和高纯度提供目标化合物。

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