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1. 发明授权

US08809557B2 Method for producing optically active fluorinated oxetane 有权
标题翻译：光学活性氟代氧杂环丁烷的制造方法
公开(公告)号：US08809557B2
公开(公告)日：2014-08-19
申请号：US13201171
申请日：2010-02-22
申请人： Koichi Mikami , Kohsuke Aikawa , Junpei Aida , Akihiro Ishii , Misugi Kato , Takashi Masuda
发明人： Koichi Mikami , Kohsuke Aikawa , Junpei Aida , Akihiro Ishii , Misugi Kato , Takashi Masuda
IPC分类号： C07D305/04
CPC分类号： C07D305/04 , B01J31/223 , B01J31/2409 , B01J2231/32 , B01J2531/0266 , B01J2531/46 , B01J2531/824 , C07B53/00 , C07D305/08
摘要： Disclosed is a method of producing an optically active fluorinated oxetane, which can be an important pharmaceutical or agricultural intermediate, by reaction of a fluorinated α-keto ester with an acyl alkenyl ether in the presence of a transition metal complex with an optically active ligand. This method utilizes a catalytic asymmetric synthesis process and does not require a stoichiometric amount of chiral source. It is thus possible to dramatically reduce the amount of use of the asymmetric catalyst especially when the reaction is performed at a high concentration of substrate (with the use of a small amount of reaction solvent) or in the absence of a reaction solvent (under neat conditions). Further, the target optically active fluorinated oxetane can be obtained with high yield and with very high optical purity. The product contains almost no difficult-to-separate impurity and shows high chemical purity.
摘要翻译：公开了通过氟化α-酮酯与酰基烯基醚在过渡金属配合物与光学活性配体的存在下反应，制备可以是重要的药用或农业中间体的光学活性氟化氧杂环丁烷的方法。该方法利用催化不对称合成方法，不需要化学计量的手性源。因此，可以显着地减少不对称催化剂的使用量，特别是当在高浓度的底物（使用少量的反应溶剂）下进行反应时，或者在没有反应溶剂的情况下条件）。此外，可以高产率和非常高的光学纯度获得目标光学活性氟化氧杂环丁烷。该产品几乎没有难以分离的杂质，显示出高的化学纯度。

2. 发明申请

US20110306781A1 Method for Producing Optically Active Fluorinated Oxetane 有权
标题翻译：生产光学活性氟化氧杂环丁烷的方法
公开(公告)号：US20110306781A1
公开(公告)日：2011-12-15
申请号：US13201171
申请日：2010-02-22
申请人： Koichi Mikami , Kohsuke Aikawa , Junpei Aida , Akihiro Ishii , Misugi Kato , Takashi Masuda
发明人： Koichi Mikami , Kohsuke Aikawa , Junpei Aida , Akihiro Ishii , Misugi Kato , Takashi Masuda
IPC分类号： C07D305/08
CPC分类号： C07D305/04 , B01J31/223 , B01J31/2409 , B01J2231/32 , B01J2531/0266 , B01J2531/46 , B01J2531/824 , C07B53/00 , C07D305/08
摘要： Disclosed is a method of producing an optically active fluorinated oxetane, which can be an important pharmaceutical or agricultural intermediate, by reaction of a fluorinated α-keto ester with an acyl alkenyl ether in the presence of a transition metal complex with an optically active ligand. This method utilizes a catalytic asymmetric synthesis process and does not require a stoichiometric amount of chiral source. It is thus possible to dramatically reduce the amount of use of the asymmetric catalyst especially when the reaction is performed at a high concentration of substrate (with the use of a small amount of reaction solvent) or in the absence of a reaction solvent (under neat conditions). Further, the target optically active fluorinated oxetane can be obtained with high yield and with very high optical purity. The product contains almost no difficult-to-separate impurity and shows high chemical purity.
摘要翻译：公开了通过在过渡金属络合物与光学活性配体的存在下，通过氟化α-酮酯与酰基烯基醚的反应，制备可以是重要的药物或农业中间体的光学活性氟化氧杂环丁烷的方法。该方法利用催化不对称合成方法，不需要化学计量的手性源。因此，可以显着地减少不对称催化剂的使用量，特别是当在高浓度的底物（使用少量的反应溶剂）下进行反应时，或者在没有反应溶剂的情况下条件）。此外，可以高产率和非常高的光学纯度获得目标光学活性氟化氧杂环丁烷。该产品几乎没有难以分离的杂质，显示出高的化学纯度。

3. 发明申请

US20090312574A1 Method for Producing Optically Active Fluorine-Containing Carbonyl-ene Product 有权
标题翻译：生产含活性氟的羰基产物的方法
公开(公告)号：US20090312574A1
公开(公告)日：2009-12-17
申请号：US12519959
申请日：2007-12-18
申请人： Koichi Mikami , Kohsuke Aikawa , Akihiro Ishii , Kaori Mogi , Takashi Ootsuka
发明人： Koichi Mikami , Kohsuke Aikawa , Akihiro Ishii , Kaori Mogi , Takashi Ootsuka
IPC分类号： C07C51/04
CPC分类号： C07C67/347 , C07B53/00 , C07B2200/07 , C07C67/343 , C07C69/732
摘要： An optically active, fluorine-containing carbonyl-ene product is produced by reacting a fluorine-containing α-ketoester with an alkene in the presence of a transition metal complex having an optically active ligand. There are Mode 1 of conducting this reaction in the absence of reaction solvent, Mode 2 of conducting this reaction in a solvent that is low in relative dielectric constant, and Mode 3 of conducting this reaction in a halogenated hydrocarbon-series solvent. In each of these three modes, it is possible to produce the optically active, fluorine-containing carbonyl-ene product with low cost.
摘要翻译：在具有光学活性配体的过渡金属络合物的存在下，通过使含氟α-酮酯与烯烃反应制备光学活性的含氟羰基产物。在没有反应溶剂的情况下进行该反应的方式1，在相对介电常数低的溶剂中进行该反应的方式2，以及在卤代烃系溶剂中进行该反应的方式3。在这三种模式中的每一种中，可以以低成本制造光学活性的含氟羰基产物。

4. 发明授权

US08278479B2 Method for producing optically active fluorine-containing carbonyl-ene product 有权
标题翻译：光学活性含氟羰基产物的制备方法
公开(公告)号：US08278479B2
公开(公告)日：2012-10-02
申请号：US12519959
申请日：2007-12-18
申请人： Koichi Mikami , Kohsuke Aikawa , Akihiro Ishii , Kaori Mogi , Takashi Ootsuka
发明人： Koichi Mikami , Kohsuke Aikawa , Akihiro Ishii , Kaori Mogi , Takashi Ootsuka
IPC分类号： C07C69/732
CPC分类号： C07C67/347 , C07B53/00 , C07B2200/07 , C07C67/343 , C07C69/732
摘要： An optically active, fluorine-containing carbonyl-ene product is produced by reacting a fluorine-containing α-ketoester with an alkene in the presence of a transition metal complex having an optically active ligand. There are Mode 1 of conducting this reaction in the absence of reaction solvent, Mode 2 of conducting this reaction in a solvent that is low in relative dielectric constant, and Mode 3 of conducting this reaction in a halogenated hydrocarbon-series solvent. In each of these three modes, it is possible to produce the optically active, fluorine-containing carbonyl-ene product with low cost.
摘要翻译：通过在具有光学活性配体的过渡金属络合物的存在下使含氟α-酮酯与烯烃反应来制备光学活性的含氟羰基产物。在没有反应溶剂的情况下进行该反应的方式1，在相对介电常数低的溶剂中进行该反应的方式2，以及在卤代烃系溶剂中进行该反应的方式3。在这三种模式中的每一种中，可以以低成本制造光学活性的含氟羰基产物。

5. 发明授权

US06326520B1 Optically active compound and method for producing same 失效
标题翻译：光学活性化合物及其制备方法
公开(公告)号：US06326520B1
公开(公告)日：2001-12-04
申请号：US09377688
申请日：1999-08-20
申请人： Akihiro Ishii , Koichi Mikami
发明人： Akihiro Ishii , Koichi Mikami
IPC分类号： C07C49213
CPC分类号： C07F7/1892 , B01J31/223 , B01J2231/341 , B01J2531/0266 , B01J2531/46 , C07C43/1787 , C07C45/30 , C07C49/82
摘要： The invention relates to a method for producing a novel optically active compound represented by the general formula [IV]. This method includes the step of reacting a vinyl ether with a halogenated acetaldehyde in the presence of an optically active binaphthol-titanium complex. With this, the novel optically active compound can be produced very easily. Furthermore, the novel optically active compound can easily be oxidized to a novel optically active &agr;,&bgr;-dihydrexyketone represented by the general formula [V]. These novel optically active compounds can each be used as useful intermediates. where R is a lower alkyl group or —Si(R3)3, where R3 is a lower alkyl group and three of R3 may be the same or different groups, R1 is a lower alkyl group or a substituted or unsubstituted phenyl group, R2 is hydrogen atom or a lower alkyl group or a substituted or unsubstituted phenyl group, or R1 and R2 are combined to form an alkylene group, and X is hydrogen, fluorine, chlorine or bromine with a proviso that three of said X may be the same or different atoms, but are not hydrogen at the same time.
摘要翻译：本发明涉及一种由通式[Ⅳ]表示的新的光学活性化合物的制备方法。该方法包括在光学活性联萘酚钛络合物存在下使乙烯基醚与卤代乙醛反应的步骤。由此，可以非常容易地制造新颖的光学活性化合物。此外，新的光学活性化合物可以容易地被氧化成由通式[V]表示的新的光学活性α，β-二羟基酮。这些新的光学活性化合物各自可用作有用的中间体。其中R是低级烷基或-Si（R3）3，其中R3是低级烷基，R3中的三个可以是相同或不同的基团，R1是低级烷基或取代或未取代的苯基，R 2为氢原子或低级烷基或取代或未取代的苯基，或R 1和R 2结合形成亚烷基，X为氢，氟，氯或溴条件是所述X中的三个可以是相同或不同的原子，但不是同时是氢。

6. 发明授权

US08217196B2 Process for producing α-fluoro-β-amino acids 有权
标题翻译：制备α-氟代 - 氨基酸的方法
公开(公告)号：US08217196B2
公开(公告)日：2012-07-10
申请号：US12919108
申请日：2009-04-21
申请人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
发明人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
IPC分类号： C07C227/16
CPC分类号： C07C227/16 , C07B55/00 , C07C227/32 , C07C229/20
摘要： By reacting a β-hydroxy-α-amino acid with sulfuryl fluoride (SO2F2) in the presence of an organic base, it is possible to produce an α-fluoro-β-amino acid of the formula [2]. By using a C8-12 tertiary amine having two or more alkyl groups of C3 or higher, and especially diisopropylethylamine, as the organic base, by-production of quantery ammonium salts is effectively suppressed. By applying the production process of the present invention, it is possible to very easily produce (2R)-3-(dibenzylamino)-2-fluoropropionic acid methyl ester, which is extremely important as a pharmaceutical intermediate, with high positional selectivity even on an industrial scale.
摘要翻译：通过在有机碱的存在下使β-羟基-α-氨基酸与硫酰氟（SO2F2）反应，可以制备式[2]的α-氟 - 二 - 氨基酸。通过使用具有两个以上具有3个以上的烷基的C8-12叔胺，特别是二异丙基乙胺作为有机碱，有效地抑制了副铵盐的副产物。通过应用本发明的制备方法，可以非常容易地制备作为药物中间体极其重要的（2R）-3-（二苄基氨基）-2-氟丙酸甲酯，即使在工业规模。

7. 发明申请

US20110015428A1 Process for Producing Alpha-Fluoro-Beta-Amino Acids 有权
标题翻译：生产α-氟-β-氨基酸的方法
公开(公告)号：US20110015428A1
公开(公告)日：2011-01-20
申请号：US12919108
申请日：2009-04-21
申请人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
发明人： Akihiro Ishii , Takako Yamazaki , Manabu Yasumoto , Takashi Masuda , Hideyuki Tsuruta
IPC分类号： C07C227/16
CPC分类号： C07C227/16 , C07B55/00 , C07C227/32 , C07C229/20
摘要： By reacting a β-hydroxy-α-amino acid with sulfuryl fluoride (SO2F2) in the presence of an organic base, it is possible to produce an α-fluoro-β-amino acid of the formula [2]. By using a C8-12 tertiary amine having two or more alkyl groups of C3 or higher, and especially diisopropylethylamine, as the organic base, by-production of quantery ammonium salts is effectively suppressed. By applying the production process of the present invention, it is possible to very easily produce (2R)-3-(dibenzylamino)-2-fluoropropionic acid methyl ester, which is extremely important as a pharmaceutical intermediate, with high positional selectivity even on an industrial scale.
摘要翻译：通过在有机碱的存在下使β-羟基-α-氨基酸与硫酰氟（SO2F2）反应，可以制备式[2]的α-氟 - 二 - 氨基酸。通过使用具有两个以上具有3个以上的烷基的C8-12叔胺，特别是二异丙基乙胺作为有机碱，有效地抑制了副铵盐的副产物。通过应用本发明的制备方法，可以非常容易地制备作为药物中间体极其重要的（2R）-3-（二苄基氨基）-2-氟丙酸甲酯，即使在工业规模。

8. 发明申请

US20110160477A1 Process for Producing alpha-Trifluoromethyl-alpha,beta-Unsaturated Ester 有权
标题翻译：生产α-三氟甲基-α，β-不饱和酯的方法
公开(公告)号：US20110160477A1
公开(公告)日：2011-06-30
申请号：US13060565
申请日：2009-09-24
申请人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
发明人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
IPC分类号： C07C67/327
CPC分类号： C07C67/317 , C07C67/327 , C07C69/65
摘要： An α-trifluoromethyl-α,β-unsaturated ester can be produced by reacting an α-trifluoromethyl-α-hydroxy ester with sulfuryl fluoride (SO2F2) in the presence of an organic base. It is preferable that the raw substrate has a hydrogen atom as one β-position substituent group and either an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aromatic ring group or a substituted aromatic ring group as the other β-position substituent group. It is more preferable that an ester moiety of the raw substrate is an alkyl ester. This raw substrate is readily available. Further, the desired reaction can proceed favorably with the use of this raw substrate. It is also preferable to use either 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the organic base. The desired reaction can proceed more favorably with the use of this organic base.
摘要翻译： α-三氟甲基-α，β-不饱和酯可以通过α-三氟甲基-α-羟基酯与硫酰氟（SO 2 F 2）在有机碱的存在下反应来制备。原料优选为氢原子作为一个位置取代基和烷基，取代的烷基，链烯基，取代的烯基，芳族环基或取代的芳环基作为另一个位置取代基。原料的酯部更优选为烷基酯。该原料基材容易获得。此外，期望的反应可以有利地利用该原始基底进行。还优选使用1,5-二氮杂双环[4.3.0]壬-5-烯（DBN）或1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为有机碱。使用该有机碱可以更有利地进行所需的反应。

9. 发明申请

US20110152536A1 Process for Production of Alpha-Trifluoromethyl-Beta-Substituted-Beta-Amino Acid 有权
标题翻译： α-三氟甲基-β-取代的β-氨基酸的制备方法
公开(公告)号：US20110152536A1
公开(公告)日：2011-06-23
申请号：US13002595
申请日：2009-08-27
申请人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Takashi Masuda
发明人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Takashi Masuda
IPC分类号： C07C229/08 , C07D261/02
CPC分类号： C07D261/04 , C07B53/00 , C07C229/20
摘要： α-Trifluoromethyl-β-substituted-β-amino acids can be produced by allowing α-trifluoromethyl-β-substituted-α,β-unsaturated esters to react with hydroxylamine to convert α-trifluoromethyl-β-substituted-α,β-unsaturated esters into dehydrogenated closed-ring body of α-trifluoromethyl-β-substituted-β-amino acid, and by hydrogenolyzing the dehydrogenated closed-ring body. According to this production process, novel α-trifluoromethyl-β-substituted-β-amino acids which are free amino acids whose functional groups are not protected can be produced, in which β-position substituent is not limited to aromatic ring group or substituted aromatic ring group while the relative stereochemistry of α-position and β-position can be also controlled.
摘要翻译： α-三氟甲基 - 和取代的 - 氨基酸可以通过使α-三氟甲基 - 取代的α，β-不饱和酯与羟胺反应以转化α-三氟甲基 - α，β-不饱和酯转化为α-三氟甲基 - 取代的 - 氨基酸的脱氢闭环体，并通过氢化脱氢闭环体。根据该制造方法，可以制备作为官能团未被保护的游离氨基酸的新型α-三氟甲基 - 取代 - 取代的 - 氨基酸，其中，取代基不限于芳环基或取代的芳族环基团，同时也可以控制相对的立体化学位置和位置。

10. 发明授权

US08653295B2 Process for producing α-trifluoromethyl-α,β-unsaturated ester 有权
标题翻译： α-三氟甲基-α，β-不饱和酯的制备方法
公开(公告)号：US08653295B2
公开(公告)日：2014-02-18
申请号：US13060565
申请日：2009-09-24
申请人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
发明人： Akihiro Ishii , Manabu Yasumoto , Takako Yamazaki , Kaori Mogi , Kazunori Mori , Takashi Masuda
IPC分类号： C07C69/76
CPC分类号： C07C67/317 , C07C67/327 , C07C69/65
摘要： An α-trifluoromethyl-α,β-unsaturated ester can be produced by reacting an α-trifluoromethyl-α-hydroxy ester with sulfuryl fluoride (SO2F2) in the presence of an organic base. It is preferable that the raw substrate has a hydrogen atom as one β-position substituent group and either an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aromatic ring group or a substituted aromatic ring group as the other β-position substituent group. It is more preferable that an ester moiety of the raw substrate is an alkyl ester. This raw substrate is readily available. Further, the desired reaction can proceed favorably with the use of this raw substrate. It is also preferable to use either 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the organic base. The desired reaction can proceed more favorably with the use of this organic base.
摘要翻译： α-三氟甲基-α，β-不饱和酯可以通过在有机碱存在下使α-三氟甲基-α-羟基酯与硫酰氟（SO 2 F 2）反应来制备。原料优选为具有作为一个β位取代基的氢原子，烷基，取代烷基，链烯基，取代烯基，芳香环基或取代芳环基作为其他β位取代基。原料的酯部更优选为烷基酯。该原料基材容易获得。此外，期望的反应可以有利地利用该原始基底进行。还优选使用1,5-二氮杂双环[4.3.0]壬-5-烯（DBN）或1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）作为有机碱。使用该有机碱可以更有利地进行所需的反应。

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