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Method for synthesis of keto acids or amino acids by hydration of acetylene compound

外国特許コード F110005533
整理番号 N061-04WO
掲載日 2011年9月7日
出願国 アメリカ合衆国
出願番号 06649106
公報番号 20090216044
公報番号 8153839
出願日 平成18年9月13日(2006.9.13)
公報発行日 平成21年8月27日(2009.8.27)
公報発行日 平成24年4月10日(2012.4.10)
国際出願番号 JP2006318199
国際公開番号 WO2007032409
国際出願日 平成18年9月13日(2006.9.13)
国際公開日 平成19年3月22日(2007.3.22)
優先権データ
  • 特願2005-267461 (2005.9.14) JP
  • 2006WO-JP318199 (2006.9.13) WO
発明の名称 (英語) Method for synthesis of keto acids or amino acids by hydration of acetylene compound
発明の概要(英語) (US8153839)
An object of the present invention is to provide a method for synthesis of keto acids by hydration of an acetylene compound (acetylene-carboxylic acids) under mild conditions free from harmful mercury catalysts and a method for synthesis of amino acids from acetylene-carboxylic acids in a single container (one-pot or tandem synthesis).
In one embodiment of the method according to the present invention for synthesis of keto acids, acetylene-carboxylic acids is hydrated in the presence of a metal salt represented by General Formula (1), where M1 represents an element in Group VIII, IX, or X of the periodic table, and X1, X2, or X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k×m=L×n.
特許請求の範囲(英語) [claim1]
1. A method for synthesis of keto acids, comprising the step of hydrating acetylene-carboxylic acids in the presence of a metal salt represented by General Formula (1),

where M1 represents Ru, Rh or Ir, and X1, X2, and X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=Lx n.
[claim2]
2. The method as set forth in claim 1, wherein the hydration is performed in the presence of an organic solvent which is inert in reaction.
[claim3]
3. The method set forth in claim 1, comprising the step of hydrating acetylene-carboxylic acids in the presence of the metal salt represented by General Formula (1), and at least one selected from a group consisting of a transition metal complex represented by General Formula (2), a transition metal complex represented by General Formula (3), and a transition metal complex represented by General Formula (8),

where M1 represents Ru, Rh or Ir, and X1, X2, and X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=L * n,

where each of R1 and R2 independently represents a hydrogen atom or a C1 to C6 lower alkyl group, and M2 represents Ru or Rh, and X1 and X2 ligand represents H2O, halogen, a solvent molecule, or nitrous ligand, and X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=L * n,

where each of R1, R2, R3, R4, and R5 independently represents a hydrogen atom or a C1 to C6 lower alkyl group, and M3 represents Ru, Rh or Ir, and each of X1 and X2 represents nitrous ligand, and X3 represents a hydrogen atom, a carboxylic acid residue, or H2O, and X1 and X2 may be bonded to each other, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=L * n,

where each of R1, R2, R3, R4, R5 and R6 independently represents a hydrogen atom or a C1 to C6 lower alkyl group, and M represents Ru, and each of X1, X2 and X3 represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=L * n.
[claim4]
4. The method as set forth in claim 3, wherein the hydration is performed in the presence of an organic solvent which is inert in reaction.
[claim5]
5. A method for synthesis of amino acids, comprising the steps of: hydrating acetylene-carboxylic acids in the presence of a metal salt whose central metal element is Ru and which is represented by General Formula (1); and
adding a transition metal complex whose central metal element is Ru and which is represented by General Formula (3) and a hydrogen and nitrogen atom donor to a reaction system of the hydrated acetylene-carboxylic acids so as to cause a reaction thereof,

where M1 represents Ru, Rh or Ir, and X1 and X2 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=L * n,

where each of R1, R2, R3, R4, and R5 independently represents a hydrogen atom or a C1 to C6 lower alkyl group, and M3 represents Ru, Rh or Ir, and each of X1 and X2 represents nitrous ligand, and X3 represents a hydrogen atom, a carboxylic acid residue, or H2O, and X1 and X2 may be bonded to each other, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=L * n.
[claim6]
6. A method for synthesis of amino acids, comprising the steps of: hydrating acetylene-carboxylic acids in the presence of a metal salt whose central metal element is Ru and which is represented by General Formula (1); and
adding organic ligand respectively represented by General Formula (4) and General Formula (5) and a hydrogen and nitrogen atom donor to a reaction system of the hydrated acetylene-carboxylic acids so as to cause a reaction thereof,

where M1 Ru, Rh or Ir, and X1, X2, and X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k * m=L * n,

where each of R1, R2, R3, R4, and R5 independently represents a hydrogen atom or a C1 to C6 lower alkyl group,

where each of R1, R2, R3, R4, R5, R6, R7, and R8 independently represents a hydrogen atom or a C1 to C6 lower alkyl group.
  • 発明者/出願人(英語)
  • OGO SEIJI
  • FUKUZUMI SHUN-ICHI
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • B01J031/18B2
  • B01J031/22D6
  • C07C051/373
  • C07C067/313
  • C07C227/04
  • C07C229/08
  • L01J531/02F2D
  • L01J531/82B
  • L01J531/82D
参考情報 (研究プロジェクト等) CREST Creation of Nano-Structured Catalysts and Materials for Environmental Conservation AREA
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