公开(公告)号：US20060135802A1

公开(公告)日：2006-06-22

申请号：US10560176

申请日：2004-06-09

申请人： Yasumasa Hamada ,  Tomoyuki Hasegawa ,  Toshiaki Matsui ,  Eiji Kasamatsu

发明人： Yasumasa Hamada ,  Tomoyuki Hasegawa ,  Toshiaki Matsui ,  Eiji Kasamatsu

IPC分类号： C07C51/15

CPC分类号： C07C53/128 ,  C07B2200/07 ,  C07C231/06 ,  C07C309/73

摘要： The present invention relates to a process for producing (2R)-2-propyloctanoic acid, which comprises subjecting (2R)-2-hexyloxirane to a two-carbon adding reaction with ring-opening reaction, followed by a protecting reaction of a hydroxyl group to convert it to a compound represented by formula (I): (wherein X represents an optionally protected hydroxyl group) and then subjecting the compound to a one-carbon adding reaction to convert it to (2R)-2-propyloctanamide, followed by recrystallization and hydrolysis. According to the process of the present invention, (2R)-2-propyloctanoic acid can be produced by less steps as compared with the conventional method without a dangerous reaction.

摘要翻译： 本发明涉及（2R）-2-丙基辛酸的制备方法，其包括使（2R）-2-己氧基丙烯在开环反应中进行二碳加成反应，接着进行羟基的保护反应 将其转化为由式（I）表示的化合物：（其中X表示任选保护的羟基），然后使化合物进行一碳加成反应，将其转化为（2R）-2-丙基辛酰胺，然后重结晶 和水解。 根据本发明的方法，与没有危险反应的常规方法相比，可以通过较少的步骤制备（2R）-2-丙氧基辛酸。

公开(公告)号：US07589221B2

公开(公告)日：2009-09-15

申请号：US10560176

申请日：2004-06-09

申请人： Yasumasa Hamada ,  Tomoyuki Hasegawa ,  Toshiaki Matsui ,  Eiji Kasamatsu

发明人： Yasumasa Hamada ,  Tomoyuki Hasegawa ,  Toshiaki Matsui ,  Eiji Kasamatsu

IPC分类号： C07B53/00 ,  C07C231/00 ,  C07C227/00

CPC分类号： C07C53/128 ,  C07B2200/07 ,  C07C231/06 ,  C07C309/73

摘要： The present invention relates to a process for producing (2R)-2-propyloctanoic acid, which comprises subjecting (2R)-2-hexyloxirane to a two-carbon adding reaction with ring-opening reaction, followed by a protecting reaction of a hydroxyl group to convert it to a compound represented by formula (I): (wherein X represents an optionally protected hydroxyl group) and then subjecting the compound to a one-carbon adding reaction to convert it to (2R)-2-propyloctanamide, followed by recrystallization and hydrolysis. According to the process of the present invention, (2R)-2-propyloctanoic acid can be produced by less steps as compared with the conventional method without a dangerous reaction.

摘要翻译： 本发明涉及（2R）-2-丙基辛酸的制备方法，其包括使（2R）-2-己氧基丙烯在开环反应中进行二碳加成反应，接着进行羟基的保护反应 将其转化为由式（I）表示的化合物：（其中X表示任选保护的羟基），然后使化合物进行一碳加成反应，将其转化为（2R）-2-丙基辛酰胺，然后重结晶 和水解。 根据本发明的方法，与没有危险反应的常规方法相比，可以通过较少的步骤制备（2R）-2-丙氧基辛酸。

公开(公告)号：US07799941B2

公开(公告)日：2010-09-21

申请号：US10563763

申请日：2004-07-09

申请人： Yasumasa Hamada ,  Kazuishi Makino

发明人： Yasumasa Hamada ,  Kazuishi Makino

IPC分类号： C07C229/08

CPC分类号： C07C227/32 ,  B01J31/2404 ,  B01J2531/821 ,  C07B2200/07 ,  C07C229/22

摘要： There is provided a process for efficiently producing an anti form of an optically active β-hydroxy-α-aminocarboxylic acid derivative that is useful as an intermediate for pharmaceuticals and agrochemicals. The process for producing optically active β-hydroxy-α-aminocarboxylic acid derivative of formula (2) or (3) wherein R1 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, R2 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, characterized by comprising subjecting an α-aminoacyl acetic acid ester compound of formula (1) wherein R1 and R2 have the same meaning as the above, to hydrogenation by catalytic asymmetric hydrogenation in the presence of an acid.

摘要翻译： 提供了有效地制备可用作药物和农业化学品中间体的光学活性的α-羟基-α-氨基羧酸衍生物的抗形式的方法。 制备式（2）或（3）的光学活性的α-羟基-α-氨基羧酸衍生物的方法，其中R 1为取代或未取代的C 1-20烷基或取代或未取代的C 4-12芳基，R 2为取代 或未取代的C 1-20烷基，或取代或未取代的C 4-12芳族基团，其特征在于包括使其中R 1和R 2具有与上述相同含义的式（1）的α-氨基酰基乙酸酯化合物氢化为 在酸存在下进行催化不对称氢化。

公开(公告)号：US20060167300A1

公开(公告)日：2006-07-27

申请号：US10563763

申请日：2004-07-09

申请人： Yasumasa Hamada ,  Kazuishi Makino

发明人： Yasumasa Hamada ,  Kazuishi Makino

IPC分类号： C07C227/14

CPC分类号： C07C227/32 ,  B01J31/2404 ,  B01J2531/821 ,  C07B2200/07 ,  C07C229/22

摘要： There is provided a process for efficiently producing an anti form of an optically active β-hydroxy-α-aminocarboxylic acid derivative that is useful as an intermediate for pharmaceuticals and agrochemicals. The process for producing optically active β-hydroxy-α-aminocarboxylic acid derivative of formula (2) or (3) wherein R1 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, R2 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, characterized by comprising subjecting an α-aminoacyl acetic acid ester compound of formula (1) wherein R1 and R2 have the same meaning as the above, to hydrogenation by catalytic asymmmetric hydrogenation in the presence of an acid.

摘要翻译： 提供了一种有效地制备可用作药物和农药的中间体的光学活性β-羟基-α-氨基羧酸衍生物的抗形式的方法。 制备式（2）或（3）的光学活性β-羟基-α-氨基羧酸衍生物的方法，其中R 1是取代或未取代的C 1-20烷基 基团或取代或未取代的C 4-12芳族基团，R 2是取代或未取代的C 1-20烷基，或取代或未取代的C 1〜 未取代的C 4-12芳族基团，其特征在于包括使式（1）的α-氨基酰基乙酸酯化合物（其中R 1和R 2） SUP>具有与上述相同的含义，在酸存在下通过催化无定形氢化进行氢化。

公开(公告)号：US20080139825A1

公开(公告)日：2008-06-12

申请号：US11795035

申请日：2006-01-12

申请人： Yasumasa Hamada ,  Kazuishi Makino

发明人： Yasumasa Hamada ,  Kazuishi Makino

IPC分类号： C07C227/30 ,  C07D317/44 ,  C07D307/02 ,  C07D333/32

CPC分类号： C07C227/32 ,  B01J31/2409 ,  B01J2231/643 ,  B01J2531/0266 ,  B01J2531/822 ,  C07D307/54 ,  C07D317/60 ,  C07D333/16 ,  C07C229/36

摘要： There is provided a process for efficiently producing an anti form of an optically active β-hydroxy-α-aminocarboxylic acid derivative that is useful as an intermediate for pharmaceuticals and agrochemicals. The process for producing optically active β-hydroxy-α-aminocarboxylic acid derivative of formula (2) or (3) therein R1 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, R2 is substituted or unsubstituted C1-20, alkyl group, or substituted or unsubstituted C4-12 aromatic group, comprising subjecting an α-aminoacyl acetic acid ester compound of formula (1) wherein R1 and R2 have the same meaning as the above, to hydrogenation by catalytic asymmetric hydrogenation in the presence of an acid by using as a catalyst a rhodium complex containing as a ligand an optically active compound of formula (4), (4′) or (5) characterized in that the hydrogenation is conducted in the presence of an acetic acid salt.

摘要翻译： 提供了一种有效地制备可用作药物和农药的中间体的光学活性β-羟基-α-氨基羧酸衍生物的抗形式的方法。 式（2）或（3）的光学活性β-羟基-α-氨基羧酸衍生物的方法其中R 1是取代或未取代的C 1-12烷基 基团或取代或未取代的C 4-12芳族基团，R 2是取代或未取代的C 1-20，烷基或取代的 或未取代的C 4-12芳族基团，其包括将其中R 1和R 2各自的式（1）的α-氨基酰基乙酸酯化合物 通过使用含有式（4），（4'）或（5）的光学活性化合物作为配体的铑络合物作为催化剂，在酸存在下通过催化不对称氢化进行氢化反应 ），其特征在于氢化在乙酸盐的存在下进行。

公开(公告)号：US07781609B2

公开(公告)日：2010-08-24

申请号：US11795035

申请日：2006-01-12

申请人： Yasumasa Hamada ,  Kazuishi Makino

发明人： Yasumasa Hamada ,  Kazuishi Makino

IPC分类号： C07C229/00

CPC分类号： C07C227/32 ,  B01J31/2409 ,  B01J2231/643 ,  B01J2531/0266 ,  B01J2531/822 ,  C07D307/54 ,  C07D317/60 ,  C07D333/16 ,  C07C229/36

摘要： There is provided a process for efficiently producing an anti form of an optically active β-hydroxy-α-aminocarboxylic acid derivative that is useful as an intermediate for pharmaceuticals and agrochemicals. The process for producing optically active β-hydroxy-α-aminocarboxylic acid derivative of formula (2) or (3) therein R1 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, R2 is substituted or unsubstituted C1-20 alkyl group, or substituted or unsubstituted C4-12 aromatic group, comprising subjecting an α-aminoacyl acetic acid ester compound of formula (1) wherein R1 and R2 have the same meaning as the above, to hydrogenation by catalytic asymmetric hydrogenation in the presence of an acid by using as a catalyst a rhodium complex containing as a ligand an optically active compound of formula (4), (4′) or (5) characterized in that the hydrogenation is conducted in the presence of an acetic acid salt.

摘要翻译： 提供了有效地制备可用作药物和农业化学品中间体的光学活性的α-羟基-α-氨基羧酸衍生物的抗形式的方法。 其中R 1为式（2）或（3）的光学活性的α-羟基-α-氨基羧酸衍生物的制备方法是取代或未取代的C 1-20烷基，或取代或未取代的C 4-12芳基，R 2取代 或未取代的C 1-20烷基，或取代或未取代的C 4-12芳族基团，包括使其中R 1和R 2具有与上述相同含义的式（1）的α-氨基酰基乙酸酯化合物经催化不对称氢化 通过使用含有作为配体的式（4），（4'）或（5）的光学活性化合物作为配体的铑络合物作为催化剂在酸存在下氢化，其特征在于氢化在乙酸存在下进行 酸盐。

公开(公告)号：US5158970A

公开(公告)日：1992-10-27

申请号：US476698

申请日：1990-02-08

申请人： Takayuki Shioiri ,  Yasumasa Hamada ,  Naoko Irako ,  Kunio Kado

发明人： Takayuki Shioiri ,  Yasumasa Hamada ,  Naoko Irako ,  Kunio Kado

IPC分类号： A61K31/40 ,  A61K31/401 ,  A61P25/28 ,  C07D207/08 ,  C07D207/16

CPC分类号： C07D207/08 ,  C07D207/16 ,  Y02P20/55

摘要： New proline derivatives of the general formula: ##STR1## wherein R stands for a lower alkyl group and X for a N-terminal protective group conventional in amino acid chemistry or an acyl group derived from an amino acid with a protective group at the N-terminal. They have inhibitory activity against prolylendopeptidase and are relatively chemically stable as compared with known compounds of this type.