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1. 发明授权

US4898822A Process for preparing optically active indoline-2-carboxylic acid 失效
标题翻译：光学活性二氢吲哚-2-羧酸的制备方法
公开(公告)号：US4898822A
公开(公告)日：1990-02-06
申请号：US846436
申请日：1986-03-31
申请人： Masanori Asada , Shigeki Hamaguchi , Hidetoshi Katsuki , Yoshio Nakamura , Hideyuki Takahashi , Kenji Takahara , Yoshio Shimada , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Masanori Asada , Shigeki Hamaguchi , Hidetoshi Katsuki , Yoshio Nakamura , Hideyuki Takahashi , Kenji Takahara , Yoshio Shimada , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C12P17/10 , C12P41/00
CPC分类号： C12P17/10 , C12P41/005 , Y10S435/83 , Y10S435/839 , Y10S435/843 , Y10S435/874 , Y10S435/897 , Y10S435/911 , Y10S435/921 , Y10S435/925
摘要： A process for preparing optically active indoline-2-carboxylic acid by an optical resolution, which comprises subjecting a racemic ester of (R,S)-indoline-2-carboxylic acid having the general formula [(R,S)-I] to the action of an enzyme or a microorganism having a stereo-selective esterase activity, which is capable of asymmetrically hydrolyzing the racemic ester [(R,S)-I] to give optically active indoline-2-carboxylic acid having the formula [II*] so as to produce the hydrolysis product, i.e. optically active indoline-2-carboxylic acid [II*] and an unreacted optically active ester of indoline-2-carboxylic acid having the general formula [I*], isolating each optically active form, and further, if necessary, hydrolyzing the obtained optically active ester [I*] to give an optical antipode of the acid [II*].According to the process of the present invention, optically active indoline-2-carboxylic acid with a high optical purity can be prepared in a simple process with a good yield.
摘要翻译：通过光学拆分制备光学活性二氢吲哚-2-羧酸的方法，其包括使具有通式[（R，S）-I]的（R，S） - 二氢吲哚-2-羧酸的外消旋酯与具有立体选择性酯酶活性的酶或微生物的作用，其能够不对称地水解外消旋酯[（R，S）-I]，得到具有式[II *]的光学活性二氢吲哚-2-羧酸， ]以产生水解产物，即具有通式[I *]的光学活性二氢吲哚-2-羧酸[II *]和未反应的二氢吲哚-2-羧酸的光学活性酯，分离每种光学活性形式，此外，如果需要，水解得到的光学活性酯[I *]，得到酸[II *]的光学对映体。根据本发明的方法，可以以简单的方法制备具有高光学纯度的光学活性二氢吲哚-2-羧酸，产率高。

2. 发明授权

US5846793A Microbial process for biotransformation to (R)-3-chloro-1,2-propanediol 失效
标题翻译：用于生物转化成（R）-3-氯-1,2-丙二醇的微生物过程
公开(公告)号：US5846793A
公开(公告)日：1998-12-08
申请号：US632663
申请日：1990-12-27
申请人： Hideyuki Takahashi , Satoru Tsuda , Yoshio Nakamura , Masahiro Ogura , Tadayoshi Shiraishi , Yoshio Shimada , Kiyoshi Watanabe
发明人： Hideyuki Takahashi , Satoru Tsuda , Yoshio Nakamura , Masahiro Ogura , Tadayoshi Shiraishi , Yoshio Shimada , Kiyoshi Watanabe
IPC分类号： C12P41/00 , C12R1/425 , C12R1/43 , C12P7/18
CPC分类号： C12P41/001
摘要： A process for preparing optically active (R)-3-chloro-1,2-propanediol, which comprises subjecting (R,S)-3-chloro-1,2-propanediol to the reaction of a microorganism belonging to genus Serratia in a reaction mixture, and then collecting the residual (R)-3-chloro-1,2-propanediol. According to the process of the present invention, (R)-3-chloro-1,2-propanediol can be efficiently prepared starting from low cost (R,S)-3-chloro-1,2-propanediol.
摘要翻译：一种制备光学活性（R）-3-氯-1,2-丙二醇的方法，其包括使（R，S）-3-氯-1,2-丙二醇在属于沙雷氏菌属的微生物的反应中反应混合物，然后收集残留的（R）-3-氯-1,2-丙二醇。根据本发明的方法，可以从低成本（R，S）-3-氯-1,2-丙二醇开始有效制备（R）-3-氯-1,2-丙二醇。

3. 发明授权

US5017484A Process for preparing 3-chloro-1,2-propanediol 失效
标题翻译：制备3-氯-1,2-丙二醇的方法
公开(公告)号：US5017484A
公开(公告)日：1991-05-21
申请号：US933822
申请日：1986-11-24
申请人： Yoshio Nakamura , Masahiro Ogura , Yoshio Shimada , Kiyoshi Watanabe , Hideyuki Takahashi
发明人： Yoshio Nakamura , Masahiro Ogura , Yoshio Shimada , Kiyoshi Watanabe , Hideyuki Takahashi
IPC分类号： C12P41/00
CPC分类号： C12P41/001 , Y10S435/822 , Y10S435/911
摘要： A process for preparing an optically active 3-chloro-1, 2-propanediol by employing microorganism which can selectively metabolize (R)- or (S)-3-chloro-1,2-propanediol. The decomposition rate of the substrate can be accelerated and the substrate concentration can be increased by adding a compound having SH group to the reaction solution.According to the process of the present invention, the optically active 3-chloro-1,2-propanediol can be easily prepared starting from low-cost (R,S)-3-chloro-1, 2-propanediol.
摘要翻译：一种通过使用可选择性代谢（R） - 或（S）-3-氯-1,2-丙二醇的微生物制备光学活性3-氯-1,2-丙二醇的方法。通过向反应溶液中加入具有SH基团的化合物，可以促进底物的分解速度，并且可以提高底物浓度。根据本发明的方法，可以从低成本（R，S）-3-氯-1,2-丙二醇开始容易地制备光学活性的3-氯-1,2-丙二醇。

4. 发明授权

US4745066A Method for producing optically active glycol derivatives 失效
标题翻译：光学活性二醇衍生物的制备方法
公开(公告)号：US4745066A
公开(公告)日：1988-05-17
申请号：US846766
申请日：1986-04-01
申请人： Shigeki Hamaguchi , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Shigeki Hamaguchi , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07B31/00 , C07C67/00 , C07C301/00 , C07C303/22 , C07C309/72 , C12P11/00 , C12P41/00 , C12R1/01 , C12R1/38 , C12R1/66 , C12R1/785 , C12R1/845
CPC分类号： C12P41/004 , C07C309/00 , C12P11/00
摘要： A method for producing optically active glycol derivatives by biochemical resolution which comprises contacting a racemic ester of the general formula 1 ##STR1## (wherein R.sub.1 is an aliphatic hydrocarbon group of 1 to 16 carbon atoms, R.sub.2 is an aliphatic hydrocarbon group of 1 to 8 carbon atoms, and R.sub.3 is an aromatic hydrocarbon group such as phenyl, tolyl or naphtyl) with a microorganism- or animal organ-derived enzyme having stereoselective hydrolytic activity to asymmetrically hydrolyze said racemic ester of general formula 1 to produce an optically active alcohol of general formula 2* ##STR2## (wherein R.sub.1 and R.sub.3 have the same meanings as defined above) and an unreacted ester of the general formula 1* ##STR3## (wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as defined hereinbefore), separating the optically active compounds from each other, hydrolyzing said ester of general formula 1* to give an optically active glycol derivative which is antipodal to the alcohol of general formula 2* and, then, isolating the same optically active glycol derivative. The invention provides a method for producing optically active glycol derivatives, which is expedient, does not require costly reagents and is suited to commercial scale production.
摘要翻译：一种通过生物化学拆分制备光学活性二醇衍生物的方法，其包括使通式1的外消旋酯1（其中R 1是1至16个碳原子的脂族烃基，R 2是1的脂族烃基， 8个碳原子，并且R 3是芳族烃基如苯基，甲苯基或萘基）与具有立体选择性水解活性的微生物或动物器官衍生的酶不对称地水解所述通式1的外消旋酯以产生光学活性的醇通式2 * 2 *（其中R 1和R 3具有与上述相同的含义）和通式1 *未反应的酯*（其中R 1，R 2和R 3具有与定义相同的含义）将光学活性化合物彼此分离，水解所述通式1 *的酯，得到对通式为醇的对映体的光学活性二醇衍生物 2 *，然后分离相同的光学活性二醇衍生物。本发明提供了一种制备光学活性二醇衍生物的方法，这是有利的，不需要昂贵的试剂并且适于商业规模生产。

5. 发明授权

US4814506A Process for preparing 3 halogeno-2-hydroxypropyltrimethylammonium halide 失效
标题翻译：制备3卤代-2-羟丙基三甲基卤化铵的方法
公开(公告)号：US4814506A
公开(公告)日：1989-03-21
申请号：US088331
申请日：1987-08-21
申请人： Kazuhiko Katayama , Shigeki Hamaguchi , Yoshikazu Kogame , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Kazuhiko Katayama , Shigeki Hamaguchi , Yoshikazu Kogame , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07C215/08 , C07C209/74 , C07C215/40 , C07C85/06
CPC分类号： C07C213/08 , C07C215/40
摘要： A process for preparing 3-halogeno-2-hydroxy-propyltrimethylammonium halide or especially one having the (S)-configuration, which comprises reacting 2,3-dihydroxypropyltrimethylammonium halide or one having the (S)-configuration, which is obtained by reacting (R)-3-halogeno-1,2-propanediol with trimethylamine, with a halogenating reagent.According to the present invention, 3-halogeno-2-hydroxypropyltrimethylammonium halide or one having the (S)-configuration, which is a useful intermediate for the synthesis of carnitine or especially (l)-carnitine, can be obtained economically, efficiently and easily.
摘要翻译：制备3-卤代-2-羟基 - 丙基三甲基卤化铵的方法，特别是具有（S） - 构型的方法，其包括使2,3-二羟基丙基三甲基卤化铵或具有（S） - 构型的反应，其通过使（ R）-3-卤代-1,2-丙二醇与三甲胺，与卤化试剂反应。根据本发明，可以经济，有效和容易地获得3-卤代-2-羟丙基三甲基卤化铵或具有（S） - 构型的化合物，其是合成肉碱或特别是（l） - 肉碱的有用中间体。

6. 发明授权

US4863859A Process for preparing optically active glycerol derivatives 失效
标题翻译：光学活性甘油衍生物的制备方法
公开(公告)号：US4863859A
公开(公告)日：1989-09-05
申请号：US822494
申请日：1986-01-27
申请人： Shigeki Hamaguchi , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Shigeki Hamaguchi , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C12P11/00 , C12P41/00
CPC分类号： C12P41/004 , C12P11/00
摘要： A process for preparing optically active glycerol derivatives by a biochemical resolution which comprises (i) subjecting an ester having the general formula [(R,S)-I]: ##STR1## wherein X is a halogen atom, R is an aliphatic hydrocarbon group of C.sub.1 to C.sub.8 and R' is an aromatic hydrocarbon group or an aliphatic hydrocarbon group of C.sub.1 to C.sub.2, to the action of enzymes derived from either microorganisms or animal organs, wherein said enzymes have a stereo selective esterase activity to asymmetrically hydrolyze the ester having the general formula [(R,S)-I] to give a mixture of an optically active alcohol having the general formula (II)*: ##STR2## wherein X and R' are as above and an optically active ester having the general formula (I)*: ##STR3## wherein X, R and R' are as above, and (ii) obtaining the optically active alcohol having the general formula (II)* and the optically active ester having the general formula (I)* by separating operations.In accordance with the present invention, there can be provided a process for preparing optically active glycerol derivatives, wherein the optically active ester having the general formula (I)* and the optically active alcohol having the general formula (II)* can be easily obtained.
摘要翻译：一种通过生化分解制备光学活性甘油衍生物的方法，其包括（i）使具有通式[（R，S）-I]的酯：其中X为卤素原子，R是C1至C8的脂族烃基，R'是C1至C2的芳族烃基或脂族烃基，来自微生物或动物器官的酶的作用，其中所述酶具有立体声选择性酯酶活性以不对称地水解具有通式[（R，S）-I]的酯，得到具有通式（II）的光学活性醇的混合物：其中X和R （I）*：其中X，R和R'如上所述，和（ii）获得具有通式（I）的光学活性酯，其具有通式（I） II）*和具有通式（I）*的光学活性酯通过分离操作。根据本发明，可以提供一种制备光学活性甘油衍生物的方法，其中可以容易地获得具有通式（I）*的光学活性酯和具有通式（II）*的光学活性醇。

7. 发明授权

US4925969A Process for preparing ethyl-alpha-amino-gamma-oxo-gamma-phenybutyrate derivatives 失效
标题翻译：制备乙基-γ-氨基-γ-氧代-γ-苯基丁酸酯衍生物的方法
公开(公告)号：US4925969A
公开(公告)日：1990-05-15
申请号：US324497
申请日：1989-03-16
申请人： Satomi Takahashi , Yasuyoshi Ueda , Kazuhiko Yamada , Yukio Yamada , Takehiko Yamane , Yoshifumi Yanagita , Yoshio Shimada , Kiyoshi Watanabe , Michio Nomura , Takehisa Ohashi , Kenji Inoue
发明人： Satomi Takahashi , Yasuyoshi Ueda , Kazuhiko Yamada , Yukio Yamada , Takehiko Yamane , Yoshifumi Yanagita , Yoshio Shimada , Kiyoshi Watanabe , Michio Nomura , Takehisa Ohashi , Kenji Inoue
IPC分类号： C07C227/08 , C07C233/46 , C07C271/06
CPC分类号： C07C233/46 , C07C227/08 , C07C271/06
摘要： Ethyl-.beta.-benzoyacrylate is reacted with an alkali metal salt of (S)-alanine or an alkali metal salt of N.sup.6 -trifluoroacetyl-L-lysine to form the corresponding Michael addition product, and not less than an equivalent amount of acid is added after completion of the Michael addition to prevent conversion of the (S,S) form of the product to the (R,S) form.
摘要翻译：乙基-β-苯甲酸酯与（S） - 丙氨酸的碱金属盐或N6-三氟乙酰基-L-赖氨酸的碱金属盐反应形成相应的迈克尔加成产物，加入不少于等量的酸完成迈克尔加成以防止（S，S）形式的产物转化为（R，S）形式。

8. 发明授权

US5003083A Process for preparing optically active cyano compound 失效
标题翻译：光学活性氰基化合物的制备方法
公开(公告)号：US5003083A
公开(公告)日：1991-03-26
申请号：US131230
申请日：1987-12-10
申请人： Kenji Inoue , Mitsunori Matsumoto , Satomi Takahashi , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Kenji Inoue , Mitsunori Matsumoto , Satomi Takahashi , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07B53/00 , B01J31/00 , B01J31/02 , C07B31/00 , C07B43/08 , C07B61/00 , C07C67/00 , C07C253/00 , C07C253/08 , C07C255/16 , C07C255/36 , C07C255/53 , C07D333/24
CPC分类号： C07C255/00 , C07D333/24
摘要： A novel process for effectively preparing an optically active cyanohydrin comprising asymmetrically cyanating an aldehyde by reacting the aldehyde with a cyanating agent in the presence of a titanate of an optically active tartaric acid derivative.

9. 发明授权

US4994600A Process for preparing trans-.beta.-benzoylacrylic acid ester 失效
标题翻译：反式β-苯甲酰丙烯酸酯的制备方法
公开(公告)号：US4994600A
公开(公告)日：1991-02-19
申请号：US869782
申请日：1986-06-02
申请人： Satomi Takahashi , Yasuyoshi Ueda , Yoshifumi Yanagida , Namito Yoshio , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Satomi Takahashi , Yasuyoshi Ueda , Yoshifumi Yanagida , Namito Yoshio , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07C69/738 , B01J27/02 , B01J31/02 , B01J31/14 , C07B61/00 , C07C67/327
CPC分类号： C07C67/327
摘要： A process for preparing trans-.beta.-benzoylacrylic acid ester having the general formula (I): ##STR1## wherein R is alkyl group or aralkyl group, which comprises dealcoholizing .beta.-benzoyl-.alpha.-alkoxypropionic acid ester having the general formula (II): ##STR2## wherein R is above, in the presence of an acid catalyst to give trans-.beta.-benzoylacrylic acid ester having the general formula (I).According to the process of the present invention, the by-product (II) produced in the esterification reaction of .beta.-benzoylacrylic acid (III) with the alcohol (V) by the dehydration reaction can be converted into the compound (I) by the dealcoholization reaction in the presence of the acid catalyst and thus trans-.beta.-benzoylacrylic acid ester (I) with a high purity can be produced in an industrially advantageous manner.
摘要翻译：制备具有通式（I）的反式-β-苯甲酰基丙烯酸酯的方法：其中R是烷基或芳烷基，其包括使具有通式（I）的β-苯甲酰基-α-烷氧基丙酸酯脱醇（II）：其中R在上面，在酸催化剂存在下，得到具有通式（I）的反式-β-苯甲酰基丙烯酸酯。根据本发明的方法，通过脱水反应在β-苯甲酰基丙烯酸（III）与醇（V）的酯化反应中产生的副产物（II）可以通过在酸催化剂存在下脱醇反应，从而可以以工业上有利的方式生产具有高纯度的反式-β-苯甲酰基丙烯酸酯（I）。

10. 发明授权

US4914199A Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives 失效
公开(公告)号：US4914199A
公开(公告)日：1990-04-03
申请号：US156873
申请日：1988-02-18
申请人： Isao Sada , Kazunori Kan , Noboru Ueyama , Shingo Matsumoto , Takehisa Ohashi , Kiyoshi Watanabe
发明人： Isao Sada , Kazunori Kan , Noboru Ueyama , Shingo Matsumoto , Takehisa Ohashi , Kiyoshi Watanabe
IPC分类号： C07D205/08 , C07F7/18
CPC分类号： C07F7/186 , C07D205/08 , Y02P20/55
摘要： A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reactig a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as difined above and R.sup.2, R.sup.3 and R.sup.4 are the same or different and each is a lower alkyl group having 1 to 4 carbon atoms or an aralkyl group, with acetic anhydride in the presence of a base and a catalyst selected from the group consisting of an organic strong acid, a mineral acid, a Lewis acid, a halogenated acyl compound having the formula (IV):R.sup.8 --CO--X (IV)wherein R.sup.8 is an alkyl group, an aralkyl group or phenyl group and X is a halogen atom, a halogenated sulfonyl compound having the formula (V):R.sup.9 --SO.sub.2 --X (V)wherein R.sup.9 is an alkyl group, an aralkyl group or phenyl group and X is a halogen atom, and a compound having the formula (VI):(R.sup.10).sub.4-n --Si(X').sub.n (VI)wherein R.sup.10 is a lower alkyl group having 1 to 6 carbon atoms or phenyl group, X' is a halogen atom or CF.sub.3 SO.sub.2 O group and n is an integer of 1 to 4. According to the present invention, there can be obtained 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives, which are useful intermediates for preparing carbapenem .beta.-lactam antibiotics, in high yield.

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