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    • 3. 发明公开
    • METHOD FOR PRODUCING N-SUBSTITUTED-2-AMINO-4-(HYDROXYMETHYLPHOSPHINYL)-2-BUTENOIC ACID
    • VERFAHREN ZUR HERSTELLUNG VON N-SUBSTITUIERTER 2-氨基-4-(羟甲基膦酰基 - ) - 2-BUTENSÄURE
    • EP2522673A1
    • 2012-11-14
    • EP11795718.3
    • 2011-06-14
    • Meiji Seika Pharma Co., Ltd.
    • ANDO, TakashiMINOWA, NobutoMITOMI, Masaaki
    • C07F9/30C07B61/00
    • C07F9/302C07F9/301
    • Provided is a method for producing a compound expressed by the following formula (3):

      [where R 1 represents a hydrogen atom or C 1-4 alkyl group, and R 2 represents C 1-4 alkyl group, C 1-4 alkoxy group, aryl group, aryloxy group or benzyloxy group], the method comprising a reaction of dehydro-condensing a compound expressed by the following formula (1):

      [where R 1 represents the same meaning as defined above], and a compound expressed by the following formula (2):

      [where R 2 represents the same meaning as defined above], while being converted to a desired geometric isomer in the presence or absence of an acid catalyst, under a condition that an organic solvent to be used for the reaction is a mixed solvent of acetic acid and a solvent selected from the group consisting of toluene, xylene and chlorobenzene, and a mixing ratio of acetic acid to the other solvent is from 1:3 to 1:5 in volume, wherein the reaction is conducted under heating and refluxing.
    • 提供由下式(3)表示的化合物的制造方法:[式中,R 1表示氢原子或C 1-4烷基,R 2表示C 1-4烷基,C 1-4烷氧基 ,芳基,芳氧基或苄氧基),所述方法包括使由下式(1)表示的化合物脱氢缩合的反应:[其中R 1表示与上述相同的含义] 在下式(2)中:[其中R 2表示与上述相同的含义],同时在存在或不存在酸催化剂的情况下,在用于反应的有机溶剂的条件下转化为所需的几何异构体 是乙酸和选自甲苯,二甲苯和氯苯的溶剂的混合溶剂,乙酸与其它溶剂的混合比例为1:3至1:5,其中反应进行 在加热和回流下。
    • 8. 发明授权
    • METHOD FOR PRODUCING L-2-AMINO-4-(HYDROXYMETHYLPHOSPHINYL)- BUTANOIC ACID
    • 制备L-2-氨基-4-(羟基甲基膦酰基) - 丁酸的方法
    • EP1864989B1
    • 2012-07-18
    • EP06730167.1
    • 2006-03-28
    • Meiji Seika Pharma Co., Ltd.
    • MINOWA, NobutoNAKANISHI, NozomuMITOMI, Masaaki
    • C07F9/30C07B53/00C07F9/6568
    • C07B53/00C07F9/301C07F9/65683
    • Disclosed is a method for efficiently and highly selectively producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, which is useful as a herbicide, through a catalytic asymmetric synthesis reaction. Specifically disclosed is a method for producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid which is characterized in that a dehydroamino acid is subjected to an asymmetric hydrogenation by using a rhodium catalyst represented by the formula (2) below and having an optically active cyclic phosphine ligand, and then the resulting product is subjected to a hydrolysis. [Rh(R4)(L)]X (2) [In the formula, R4 represents 1,5-cyclooctadien or norbornadien; L represents a substance represented by the following formula (6): [Chemical formula 1] (6) (wherein R5 and R8 respectively represent a C1-4 alkyl group; R6 and R7 respectively represent a hydrogen atom or a hydroxyl group; and Y represents a group selected from groups represented by the following formula (7): [Chemical formula 2] (7) (wherein Me represents a methyl group).]
    • 本发明公开了一种通过催化不对称合成反应有效且高度选择性地制备作为除草剂有用的L-2-氨基-4-(羟甲基氧膦基) - 丁酸的方法。 具体公开了一种制备L-2-氨基-4-(羟甲基氧膦基) - 丁酸的方法,其特征在于通过使用由下式(2)表示的铑催化剂使脱氢氨基酸进行不对称氢化,并且具有 光学活性的环膦配体,然后将所得产物进行水解。 [Rh(R4)(L)] X(2)[式中,R4表示1,5-环辛二烯或降冰片二烯; L表示由下式(6)表示的物质:[化学式1](6)(其中R5和R8分别表示C1-4烷基; R6和R7分别表示氢原子或羟基; Y 表示选自由下式(7)表示的基团的基团:[化学式2](7)(其中Me表示甲基)]