公开(公告)号：US20090270647A1

公开(公告)日：2009-10-29

申请号：US12442011

申请日：2007-09-19

申请人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

发明人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

IPC分类号： C07F9/32

CPC分类号： C07B53/00 ,  B01J31/0207 ,  B01J31/0209 ,  B01J31/0235 ,  B01J31/0237 ,  B01J31/0261 ,  B01J31/0271 ,  B01J2231/341 ,  C07F9/3211 ,  Y02P20/55

摘要： A method for efficiently producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, useful as a herbicide, by a catalytic asymmetric synthesis reaction with a high asymmetric yield. The method includes a step in which a compound represented by the below formula (1) and a benzylamine are reacted in the presence of dehydrating agent, then the resulting mass is reacted with hydrogen cyanide in the presence of an asymmetric catalyst, followed by acid hydrolysis, further followed by elimination of a protective group. [chemical formula 1] (1) (where, R1 represents a C1-4 alkyl group.)

摘要翻译： 通过具有高不对称产率的催化不对称合成反应有效生产可用作除草剂的L-2-氨基-4-（羟甲基氧膦基） - 丁酸的方法。 该方法包括在脱水剂的存在下使由下式（1）表示的化合物和苄胺反应的步骤，然后将所得物质与氰化氢在不对称催化剂的存在下反应，随后进行酸水解 ，然后除去保护基。 [化学式1]（1）（其中，R 1表示C 1-4烷基）

公开(公告)号：US08017797B2

公开(公告)日：2011-09-13

申请号：US12530022

申请日：2008-03-21

申请人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

发明人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

IPC分类号： C07C67/00

CPC分类号： C07F9/301

摘要： A method for efficiently producing 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid, useful as a production intermediate of herbicide L-AMPB. The method comprises using a compound represented by the below formula (4): (4) where R1 represents a C1-4 alkyl group, arylmethyl group, or substituted arylmethyl group.

摘要翻译： 一种有效生产4-（羟甲基氧膦基）-2-氧代丁酸的方法，可用作除草剂L-AMPB的生产中间体。 该方法包括使用由下式（4）表示的化合物：（4）其中R1表示C1-4烷基，芳基甲基或取代的芳基甲基。

公开(公告)号：US20080146837A1

公开(公告)日：2008-06-19

申请号：US11909839

申请日：2006-03-28

申请人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

发明人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

IPC分类号： C07F9/36

CPC分类号： C07B53/00 ,  C07F9/301 ,  C07F9/65683

摘要： 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 hydrolysis: [Rh(R4)(L)]X   (2) [where R4 represents 1,5-cyclooctadien or norbornadien; L represents a substance represented by the following formula (6): (wherein R5 and R8 respectively represent a C1-4 alkyl group; R6 and R7 respectively represent hydrogen atom or hydroxyl group; and Y represents a group selected from groups represented by the following formula (7): (where Me represents methyl group)).].

摘要翻译： 公开了通过催化不对称合成反应有效和高选择性地生产可用作除草剂的L-2-氨基-4-（羟甲基氧膦基） - 丁酸的方法。 具体公开了一种生产L-2-氨基-4-（羟甲基氧膦基） - 丁酸的方法，其特征在于，使用下式（2）表示的铑催化剂对脱氢氨基酸进行不对称氢化， 光学活性环膦配体，然后将所得产物进行水解：<？in-line-formula description =“In-line Formulas”end =“lead”→> [Rh（R 4） >）（L）] X（2）<？in-line-formula description =“In-line Formulas”end =“tail”？> [其中R 4表示1,5-环辛二烯或 降血统 L表示由下式（6）表示的物质：（其中R 5和R 8分别表示C 1-4烷基） ; R 6和R 7分别表示氢原子或羟基; Y表示选自下式（7）表示的基团：（其中Me表示甲基 组））。]。

公开(公告)号：US07795464B2

公开(公告)日：2010-09-14

申请号：US12442011

申请日：2007-09-19

申请人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

发明人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

IPC分类号： C07F9/32

CPC分类号： C07B53/00 ,  B01J31/0207 ,  B01J31/0209 ,  B01J31/0235 ,  B01J31/0237 ,  B01J31/0261 ,  B01J31/0271 ,  B01J2231/341 ,  C07F9/3211 ,  Y02P20/55

摘要： A method for efficiently producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, useful as a herbicide, by a catalytic asymmetric synthesis reaction with a high asymmetric yield. The method includes a step in which a compound represented by the below formula (1) and a benzylamine are reacted in the presence of dehydrating agent, then the resulting mass is reacted with hydrogen cyanide in the presence of an asymmetric catalyst, followed by acid hydrolysis, further followed by elimination of a protective group. [chemical formula 1] (1) (where, R1 represents a C1-4 alkyl group).

摘要翻译： 通过具有高不对称产率的催化不对称合成反应有效生产可用作除草剂的L-2-氨基-4-（羟甲基氧膦基） - 丁酸的方法。 该方法包括在脱水剂的存在下使由下式（1）表示的化合物和苄胺反应的步骤，然后将所得物质与氰化氢在不对称催化剂的存在下反应，随后进行酸水解 ，然后除去保护基。 [化学式1]（1）（其中，R1表示C1-4烷基）。

公开(公告)号：US20100063313A1

公开(公告)日：2010-03-11

申请号：US12530022

申请日：2008-03-21

申请人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

发明人： Nobuto Minowa ,  Nozomu Nakanishi ,  Masaaki Mitomi

IPC分类号： C07C69/52 ,  C07C53/00

CPC分类号： C07F9/301

摘要： A method for efficiently producing 4-(hydroxymethylphosphinyl)-2-oxobutanoic acid, useful as a production intermediate of herbicide L-AMPB. The method comprises using a compound represented by the below formula (4): (4) where R1 represents a C1-4 alkyl group, arylmethyl group, or substituted arylmethyl group.

摘要翻译： 一种有效生产4-（羟甲基氧膦基）-2-氧代丁酸的方法，可用作除草剂L-AMPB的生产中间体。 该方法包括使用由下式（4）表示的化合物：（4）其中R1表示C1-4烷基，芳基甲基或取代的芳基甲基。

公开(公告)号：US20120316358A1

公开(公告)日：2012-12-13

申请号：US13579135

申请日：2011-06-14

申请人： Takashi Ando ,  Nobuto Minowa ,  Masaaki Mitomi

发明人： Takashi Ando ,  Nobuto Minowa ,  Masaaki Mitomi

IPC分类号： C07F9/30

CPC分类号： C07F9/302 ,  C07F9/301

摘要： Provided is a method for producing a compound expressed by the following formula (3): [where R1 represents a hydrogen atom or C1-4 alkyl group, and R2 represents C1-4 alkyl group, C1-4 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) and a compound expressed by the following formula (2): 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.

摘要翻译： 本发明提供由下式（3）表示的化合物的制造方法：[式中，R1表示氢原子或C1-4烷基，R2表示C1-4烷基，C1-4烷氧基，芳基，芳氧基 基团或苄氧基]，该方法包括使由下式（1）表示的化合物与下式（2）表示的化合物脱氢缩合的反应：在存在或不存在下转化为所需的几何异构体 的酸催化剂，在用于反应的有机溶剂是乙酸和选自甲苯，二甲苯和氯苯的溶剂的混合溶剂的条件下进行。

公开(公告)号：US08481779B2

公开(公告)日：2013-07-09

申请号：US13579135

申请日：2011-06-14

申请人： Takashi Ando ,  Nobuto Minowa ,  Masaaki Mitomi

发明人： Takashi Ando ,  Nobuto Minowa ,  Masaaki Mitomi

IPC分类号： C07F9/30

CPC分类号： C07F9/302 ,  C07F9/301

摘要： Provided is a method for producing a compound expressed by the following formula (3): [where R1 represents a hydrogen atom or C1-4 alkyl group, and R2 represents C1-4 alkyl group, C1-4 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) and a compound expressed by the following formula (2): 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.

摘要翻译： 本发明提供由下式（3）表示的化合物的制造方法：[式中，R1表示氢原子或C1-4烷基，R2表示C1-4烷基，C1-4烷氧基，芳基，芳氧基 基团或苄氧基]，该方法包括使由下式（1）表示的化合物与下式（2）表示的化合物脱氢缩合的反应：在存在或不存在下转化为所需的几何异构体 的酸催化剂，在用于反应的有机溶剂是乙酸和选自甲苯，二甲苯和氯苯的溶剂的混合溶剂的条件下进行。

公开(公告)号：US20120330021A1

公开(公告)日：2012-12-27

申请号：US13572971

申请日：2012-08-13

申请人： Kimihiko Goto ,  Kazumi Yamamoto ,  Masayo Sakai ,  Masaaki Mitomi ,  Takashi Ando

发明人： Kimihiko Goto ,  Kazumi Yamamoto ,  Masayo Sakai ,  Masaaki Mitomi ,  Takashi Ando

IPC分类号： C07D493/04

CPC分类号： C07D493/04 ,  Y02P20/55

摘要： A process for producing compound C represented by formula C is disclosed: wherein R′ represents substituent groups as described herein. The process can produce pyripyropene derivatives that have acyloxy groups at the 1- and 11-positions and a hydroxyl group at the 7-position and are useful as insect pest control agents at a high yield.

摘要翻译： 公开了制备由式C表示的化合物C的方法：其中R'表示如本文所述的取代基。 该方法可以产生在1-位和11位上具有酰氧基并且在7-位上具有羟基并且以高产率用作害虫控制剂的吡哆烯衍生物。

公开(公告)号：US20100160640A1

公开(公告)日：2010-06-24

申请号：US12733113

申请日：2008-08-13

申请人： Kimihiko Goto ,  Kazumi Yamamoto ,  Masayo Sakai ,  Masaaki Mitomi ,  Takashi Ando

发明人： Kimihiko Goto ,  Kazumi Yamamoto ,  Masayo Sakai ,  Masaaki Mitomi ,  Takashi Ando

IPC分类号： C07D493/04

CPC分类号： C07D493/04 ,  Y02P20/55

摘要： Disclosed is a process for producing compound C represented by formula C: wherein R′ represents straight chain, branched chain, or cyclic C2-6 alkylcarbonyl, wherein R1b is used as a protective group for hydroxyl at the 7-position of compound C. R1b represents formyl; optionally substituted straight chain C1-4 alkylcarbonyl; optionally substituted benzyl; group —SiR3R4R5 optionally substituted by halogen atom wherein R3, R4, and R5 each independently represent straight chain or branched chain C1-6 alkyl or phenyl; C1-6 alkyloxy-C1-6 alkyl optionally substituted by halogen atom; C1-6 alkylthio-C1-6 alkyl optionally substituted by halogen atom; straight chain, branched chain, or cyclic C1-4 alkyl optionally substituted by halogen atom, provided that, when alkyl in the C1-4 alkyl group is of a branched chain or cyclic type, the alkyl group is C3-4 alkyl; C2-6 alkenyl optionally substituted by halogen atom; C2-6 alkynyl optionally substituted by halogen atom; or an optionally substituted saturated or unsaturated five- or six-membered heterocyclic group. The process can produce pyripyropene derivatives that have acyloxy groups at the 1- and 11-positions and a hydroxyl group at the 7-position and are useful as insect pest control agents at a high yield.

摘要翻译： 公开了一种制备由式C表示的化合物C的方法：其中R'表示直链，支链或环状C 2-6烷基羰基，其中R 1b用作化合物C的7-位羟基保护基。R1b 代表甲酰基; 任选取代的直链C 1-4烷基羰基; 任选取代的苄基; 基团-SiR 3 R 4 R 5任选被卤素原子取代，其中R 3，R 4和R 5各自独立地表示直链或支链C 1-6烷基或苯基; 任选被卤素原子取代的C 1-6烷氧基-C 1-6烷基; 任选被卤素原子取代的C 1-6烷硫基-C 1-6烷基; 直链，支链或任选被卤素原子取代的环状C 1-4烷基，条件是当C 1-4烷基中的烷基为支链或环状时，该烷基为C 3-4烷基; 任选被卤素原子取代的C 2-6烯基; 任选被卤素原子取代的C 2-6炔基; 或任选取代的饱和或不饱和的五元或六元杂环基。 该方法可以产生在1-位和11位上具有酰氧基并且在7-位上具有羟基并且以高产率用作害虫防治剂的吡哆烯衍生物。

公开(公告)号：US08759529B2

公开(公告)日：2014-06-24

申请号：US13572971

申请日：2012-08-13

申请人： Kimihiko Goto ,  Kazumi Yamamoto ,  Masayo Sakai ,  Masaaki Mitomi ,  Takashi Ando

发明人： Kimihiko Goto ,  Kazumi Yamamoto ,  Masayo Sakai ,  Masaaki Mitomi ,  Takashi Ando

IPC分类号： C07D493/04

CPC分类号： C07D493/04 ,  Y02P20/55

摘要： A process for producing compound C represented by formula C is disclosed: wherein R′ represents substituent groups as described herein. The process can produce pyripyropene derivatives that have acyloxy groups at the 1- and 11-positions and a hydroxyl group at the 7-position and are useful as insect pest control agents at a high yield.

摘要翻译： 公开了制备由式C表示的化合物C的方法：其中R'表示如本文所述的取代基。 该方法可以产生在1-位和11位上具有酰氧基并且在7-位上具有羟基并且以高产率用作害虫防治剂的吡哆烯衍生物。