Preparation method of beta-homoglutamic acid

A high-glutamic acid, high-yield technology, applied in the preparation of carbamic acid derivatives, organic compounds, organic chemical methods, etc., can solve the problems of cumbersome preparation, high cost, and unsuitable scale-up

Inactive Publication Date: 2020-10-27
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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Problems solved by technology

At present, there are two main strategies for preparing optically pure β-homoglutamic acid: one is to use optically pure chiral auxiliary reagents for chiral induction synthesis, such as the optically pure 2-tert-butylperhydropyrimidinone induction method reported by Snieckus (J.Am. Chem.Soc.1996,118,8727), the D-gulose derived hydroxylamine induction method developed by Bode (Chem.Sci.2010,1,637.), although this strategy can successfully prepare chiral β-homoglutamic acid A variety of β-amino acids, but the chiral induction reagent used in this method is not easy to obtain,

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  • Preparation method of beta-homoglutamic acid
  • Preparation method of beta-homoglutamic acid

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[0012] (1) Preparation method of racemic β-homoglutamic acid

[0013] The synthesis of racemic β-homoglutamic acid in the present invention adopts racemic 3-cyclohexene carboxylic acid as raw material, utilizes diphenylphosphoryl azide to synthesize acyl azide, obtains isocyanate through Curtius rearrangement, and then adds benzyl alcohol Or tert-butanol or fluorene methanol one-pot reaction to generate benzyl cyclohexenyl carbamate or tert-butyl cyclohexenyl carbamate or fluorenylmethyl cyclohexenyl carbamate, and then use potassium permanganate to carry out olefin The diacid intermediate is obtained by oxidative cleavage, and the racemic β-homoglutamic acid can be obtained by removing the protecting group Cbz or Boc or Fmoc at last.

[0014] The solvents used in the Curtius rearrangement reaction are toluene and xylene, and the reaction temperature is 100° C. to 140° C.

[0015] (2) Preparation method of optically pure β-homoglutamic acid

[0016] In the present invention,...

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Abstract

The invention belongs to the field of preparation of organic compounds, and provides a preparation method of beta-homoglutamic acid. The method is characterized in that: 3-cyclohexenecarboxylic acid is used as a raw material, beta-homoglutamic acid is synthesized at a high yield through three the steps of reactions of Curtius rearrangement, olefin oxidation and protection group removal, and beta-homoglutamic acid with high yield and high optical purity can be obtained through configuration retention by using optically pure 3-cyclohexenecarboxylic acid. The method has the advantages of easily available raw materials, mild reaction conditions and low cost, and is suitable for large-scale preparation of beta-homoglutamic acid.

Description

technical field [0001] The invention belongs to the field of preparation of organic compounds. The invention relates to a method for preparing β-homoglutamic acid. Background technique [0002] β-homoglutamic acid is a very important non-natural β-amino acids. In recent years, it has been widely used in the synthesis of new peptide drugs and the development of nanomaterials, and the research on its synthesis methods has gradually been paid attention to. At present, there are two main strategies for preparing optically pure β-homoglutamic acid: one is to use optically pure chiral auxiliary reagents for chiral induction synthesis, such as the optically pure 2-tert-butylperhydropyrimidinone induction method reported by Snieckus (J.Am. Chem.Soc.1996,118,8727), the D-gulose derived hydroxylamine induction method developed by Bode (Chem.Sci.2010,1,637.), although this strategy can successfully prepare chiral β-homoglutamic acid A variety of β-amino acids, but the chiral inductio...

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Application Information

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IPC IPC(8): C07C229/24C07C227/20
CPCC07B2200/07C07C227/20C07C269/02C07C269/06C07C229/24C07C271/22C07C271/24Y02P20/55
Inventor 边广岭宋玲徐静
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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