Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids
    2.
    发明授权
    Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids 有权
    手性2-取代和3-取代羧酸的动力学分辨率

    公开(公告)号:US07767811B2

    公开(公告)日:2010-08-03

    申请号:US11447237

    申请日:2006-06-05

    摘要: One aspect of the present invention relates to a method for the kinetic resolution of racemic and diastereomeric mixtures of chiral compounds. The critical elements of the method are: a non-racemic chiral tertiary-amine-containing catalyst; a racemic or diastereomeric mixture of a chiral substrate, e.g., a cyclic carbonate or cyclic carbamate; and a nucleophile, e.g., an alcohol, amine or thiol. A preferred embodiment of the present invention relates to a method for achieving the kinetic resolution of racemic and diastereomeric mixtures of derivatives of α- and β-amino, hydroxy, and thio carboxylic acids. In certain embodiments, the methods of the present invention achieve dynamic kinetic resolution of a racemic or diastereomeric mixture of a substrate, i.e., a kinetic resolution wherein the yield of the resolved enantiomer or diastereomer, respectively, exceeds the amount present in the original mixture due to the in situ equilibration of the enantiomers or diastereomers under the reaction conditions prior to the resolution step.

    摘要翻译: 本发明的一个方面涉及手性化合物的外消旋和非对映体混合物的动力学拆分方法。 该方法的关键元素是:非外消旋手性叔胺催化剂; 手性底物,例如环状碳酸酯或环状氨基甲酸酯的外消旋或非对映体混合物; 和亲核试剂,例如醇,胺或硫醇。 本发明的一个优选实施方案涉及一种实现α-和β-氨基,羟基和硫代羧酸的衍生物的外消旋和非对映体混合物的动力学拆分的方法。 在某些实施方案中,本发明的方法实现了底物的外消旋或非对映体混合物的动态动力学拆分,即动力学拆分,其中分辨的对映异构体或非对映体的产率分别超过原始混合物中存在的量 涉及在分离步骤之前的反应条件下对映异构体或非对映异构体的原位平衡。

    Kinetic resolutions of chiral 2-and 3-substituted carboxylic acids
    5.
    发明授权
    Kinetic resolutions of chiral 2-and 3-substituted carboxylic acids 有权
    手性2-取代和3-取代羧酸的动力学分辨率

    公开(公告)号:US06743914B2

    公开(公告)日:2004-06-01

    申请号:US10300704

    申请日:2002-11-20

    IPC分类号: C07D41312

    摘要: One aspect of the present invention relates to a method for the kinetic resolution of racemic and diastereomeric mixtures of chiral compounds. The critical elements of the method are: a non-racemic chiral tertiary-amine-containing catalyst; a racemic or diastereomeric mixture of a chiral substrate, e.g., a cyclic carbonate or cyclic carbamate; and a nucleophile, e.g., an alcohol, amine or thiol. A preferred embodiment of the present invention relates to a method for achieving the kinetic resolution of racemic and diastereomeric mixtures of derivatives of &agr;- and &bgr;-amino, hydroxy, and thio carboxylic acids. In certain embodiments, the methods of the present invention achieve dynamic kinetic resolution of a racemic or diastereomeric mixture of a substrate, i.e., a kinetic resolution wherein the yield of the resolved enantiomer or diastereomer, respectively, exceeds the amount present in the original mixture due to the in situ equilibration of the enantiomers or diastereomers under the reaction conditions prior to the resolution step.

    摘要翻译: 本发明的一个方面涉及手性化合物的外消旋和非对映体混合物的动力学拆分方法。 该方法的关键元素是:非外消旋手性叔胺催化剂; 手性底物,例如环状碳酸酯或环状氨基甲酸酯的外消旋或非对映体混合物; 和亲核试剂,例如醇,胺或硫醇。 本发明的优选实施方案涉及一种实现α和β-氨基,羟基和硫代羧酸的衍生物的外消旋和非对映体混合物的动力学拆分的方法。 在某些实施方案中,本发明的方法实现了底物的外消旋或非对映体混合物的动态动力学拆分,即动力学拆分,其中分辨的对映异构体或非对映体的产率分别超过原始混合物中存在的量 涉及在分离步骤之前的反应条件下对映异构体或非对映异构体的原位平衡。

    Cage-shaped cyclobutanoic dianhydrides and process for production thereof
    9.
    发明授权
    Cage-shaped cyclobutanoic dianhydrides and process for production thereof 有权
    笼形环丁酸二酐及其生产方法

    公开(公告)号:US07872148B2

    公开(公告)日:2011-01-18

    申请号:US11665024

    申请日:2005-10-18

    IPC分类号: C07D493/08

    摘要: A process which comprises reacting a 1,2,3,4-cyclobutanetetracarboxylic-1,2:3,4-dianhydride [1] with an alcohol [2] in the presence of an acid catalyst to obtain a compound [3], isomerizing the compound [3] with a base catalyst into a compound [4], reacting the compound [4] with an organic acid to obtain a compound [5], and reacting the compound [5] with a dehydrating agent to obtain a 1,2,3,4-cyclobutanetetracarboxylic-1,3:2,4-dianhydride: wherein R1 and R2 are each independently hydrogen, halogeno, alkyl of 1 to 10 carbon atoms, halogenated alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, phenyl, or cyano; and R3 is alkyl of 1 to 10 carbon atoms.

    摘要翻译: 一种方法包括在酸催化剂存在下使1,2,3,4-环丁烷四羧酸-1,2:3,4-二酐[1]与醇[2]反应,得到化合物[3],异构化 化合物[3]与碱催化剂合成化合物[4],使化合物[4]与有机酸反应,得到化合物[5],并使化合物[5]与脱水剂反应,得到1, 2,3,4-环丁烷四羧酸-1,3:2,4-二酐:其中R1和R2各自独立地为氢,卤代,1-10个碳原子的烷基,1-10个碳原子的卤代烷基,3〜 8个碳原子,苯基或氰基; 并且R 3是1至10个碳原子的烷基。

    E2, E4, Z8-undecatrienoic acid and ester and carboxamide derivatives thereof, organoleptic uses thereof and processes for preparing same
    10.
    发明授权
    E2, E4, Z8-undecatrienoic acid and ester and carboxamide derivatives thereof, organoleptic uses thereof and processes for preparing same 有权
    E2,E4,Z8-十一碳三烯酸及其酯和羧酰胺衍生物,其感官用途及其制备方法

    公开(公告)号:US07141686B2

    公开(公告)日:2006-11-28

    申请号:US10618367

    申请日:2003-07-10

    IPC分类号: C07C231/00 C07C233/00

    摘要: Described is a genus of E2,E4,Z8-undecatrienoic acid derivatives defined according to the structure: wherein Z represents —OR″ or —NRR′ with the provisos that when Z is —OR″, R″ is hydrogen, C1–C6 straight chain or branched-chain alkyl or C3–C6 straight chain or branched-chain alkenyl; and when Z is —NRR′, R represents, in the alternative, hydrogen, methyl or ethyl and R′ represents methyl, ethyl, n-propyl, cyclopropyl, isopropyl, n-butyl, sec-butyl, isobutyl, 2-methylbutyl, cyclobutyl, cyclopentyl or allyl. The E2,E4,Z8-undecatrienoic acid derivatives are useful in imparting, augmenting and/or enhancing flavors, aromas and somatosensory effects in or to consumable materials such as foods, beverages, skin care products, oral care products, medicinal products and the like. Also described is a synthesis process for producing such derivatives.

    摘要翻译: 描述了根据以下结构定义的E2,E4,Z8-十一碳烯酸衍生物属:其中Z表示-OR“或-NRR',条件是当Z为-OR”时,R“为氢,C 直链或支链烷基或C 3 -C 6直链或支链C 1 -C 6直链或支链烷基或C 3 -C 6 - 链烯基; 当Z是-NRR'时,R代表氢,甲基或乙基,R'代表甲基,乙基,正丙基,环丙基,异丙基,正丁基,仲丁基,异丁基,2-甲基丁基, 环丁基,环戊基或烯丙基。 E2,E4,Z8-十一碳三烯酸衍生物可用于赋予,增强和/或增强食用,饮料,护肤品,口腔护理产品,药用产品等中的消耗材料中的香料,香气和体感效应 。 还描述了制备这种衍生物的合成方法。