Preparation method of chiral alpha-amino acid

An amino acid and chiral technology, which is applied in the field of preparation of chiral α-amino acids, can solve the problems of increasing the difficulty of process operation, occupying the main cost of the process, and narrow application range, so as to achieve safe, stable and reliable production, high economic benefits and social value , a wide range of effects

Inactive Publication Date: 2016-02-17
天台宜生生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(2) Although the development of chiral catalyst is rapid, its price is also very expensive. The catalytic efficiency is proportional to the amount of catalyst used, which occupies the main cost of the entire process.
(3) The more efficient the chiral catalyst, the higher the requirements for the substrate and reaction conditions, and it is very easy to cause catalyst poisoning and affect the reaction process, which increases the difficulty of process operation
(4) The scope of application of many technological routes reported at present is relatively narrow, often only suitable for the production of one or several chiral α-amino acids, with poor practicability and poor economic benefits

Method used

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  • Preparation method of chiral alpha-amino acid
  • Preparation method of chiral alpha-amino acid
  • Preparation method of chiral alpha-amino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: (S)-butanine hydrochloride

[0054] Step 1: (4Z)-Ethylene-2-phenyloxazol-5(4H)-one

[0055] Under nitrogen protection, N-benzoylglycine (0.45mol, 80.6g), anhydrous potassium acetate (0.55mol, 54.0g), acetic anhydride (2mol, 204.0g) were successively dropped into a 1L three-necked flask, and mechanically Stir for 30min. Add acetaldehyde (0.5mol, 22.0g), heat up to 65°C, and keep the temperature of the reaction system at 60-70°C. TLC tracking (developing solvent is n-hexane: ethyl acetate = 10:1) until the raw material point reacted completely. Turn off the heating, cool down to 0-5°C in an ice bath, a large amount of yellow solid precipitates, and stand for 6 hours to crystallize. Suction filtration and vacuum drying yielded a crude yellow solid. The crude product was recrystallized from butyl acetate to obtain 54.2 g of pure product, with a yield of 64.3% and a chemical purity of 99.2%.

[0056] 1 H-NMR (CDCl 3 ,400MHz)δ8.17(d,2H,J=8.0Hz),7.31-7.6...

Embodiment 2

[0066] Embodiment 2: (S)-thienylalanine hydrochloride

[0067] Step 1: (4Z)-thiophenylidene-2-phenyl-oxazol-5(4H)-one

[0068] Under nitrogen protection, N-benzoylglycine (0.55mol, 98.5g), anhydrous sodium acetate (0.5mol, 41.0g), and acetic anhydride (1.5mol, 153.1g) were successively dropped into a 1L three-necked flask. Stir mechanically for 30 min. Add thiophene carboxaldehyde (0.5mol, 56.1g), heat to 95°C, and keep the temperature of the reaction system at 90-100°C. TLC tracking (developing solvent is n-hexane: ethyl acetate = 10:1) until the raw material point reacted completely. Turn off the heating, cool down to 0-5°C in an ice bath, a large amount of yellow solid precipitates, and stand for 6 hours to crystallize. Suction filtration and vacuum drying yielded a crude yellow solid. The crude product was recrystallized from butyl acetate to obtain 110.2 g of the pure product, with a yield of 86.3% and a chemical purity of 99.0%.

[0069] 1 H-NMR (CDCl 3 ,400MHz)...

Embodiment 3

[0079] Example 3: (S)-Phenylalanine Phosphate

[0080] Step 1: (4Z)-Phenylmethylene-2-phenyl-oxazol-5(4H)-one

[0081] Under nitrogen protection, N-benzoylglycine (0.6mol, 107.5g), anhydrous calcium acetate (0.65mol, 102.8g), and acetic anhydride (1.0mol, 102.1g) were successively dropped into a 1L three-necked flask. Stir mechanically for 30 min. Add benzaldehyde (0.5mol, 53.1g), heat to 85°C, and keep the temperature of the reaction system at 80-90°C. TLC tracking (developing solvent is n-hexane: ethyl acetate = 10:1) until the raw material point reacted completely. Turn off the heating, cool down to 0-5°C in an ice bath, a large amount of yellow solid precipitates, and stand for 6 hours to crystallize. Suction filtration and vacuum drying yielded a crude yellow solid. The crude product was recrystallized from butyl acetate to obtain 115.3 g of pure product, with a yield of 92.5% and a chemical purity of 99.3%.

[0082] 1 H-NMR (CDCl 3 ,400MHz)δ8.16(d,2H,J=8.0Hz),7....

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Abstract

The invention discloses a preparation method of chiral alpha-amino acid. Initial raw materials comprising aldehyde and N-acryl substituted glycine undergo Erlenmeyer-Plochl cyclization, hydrolysis or alcoholysis, asymmetric catalytic hydrogenation and acid hydrolysis to obtain the chiral alpha-amino acid compound. The method adopting the above synthesis route has the advantages of mild reaction conditions, simple technological operation, safe and stable production, realization of high yield, good chemical purity and good optical purity of the above obtained product, wide application range, and suitableness for industrial production.

Description

technical field [0001] The invention relates to a preparation method of chiral α-amino acid. Background technique [0002] Amino acid is the building block of protein and also a very important nutrient. It plays an irreplaceable role in the life activities of human body and animals [China Pharmaceutical Information, 2014, 30(1), 11-14.]. Optically active α-amino acids have important biological activities and physiological functions. They are important precursors for chiral drugs such as antibiotics, agricultural chemicals, food and a series of peptides. They can also be used as chiral inducers in asymmetric synthesis. . [0003] At present, the production of amino acids has become an independent industry in the world. Its main preparation methods include microbial fermentation, chemical synthesis and chemical-biological enzyme method [Fermentation Technology Communication, 2014, 43(4).]. Theoretically, almost all amino acid products can be industrially produced by microbi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/20C07C229/36C07C229/12C07D333/24C07D207/20C07D307/54
Inventor 夏建胜陈德响李坚军张敏陈龙
Owner 天台宜生生化科技有限公司
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