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Enzymatic synthesis method of (S)-2-aminobutanamide

A technology for enzymatic synthesis of aminobutyramide, which is applied in the field of enzymatic synthesis of 2-aminobutanamide, can solve the problems of few synthesis reports and low yield, and achieve the effects of short reaction route, high ee value and pollution reduction

Active Publication Date: 2021-01-08
江苏八巨药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such as utilizing nitrile hydratase to hydrate 2-aminobutyronitrile stereoselectively, thereby obtaining S-2-aminobutanamide, the yield and optical purity reach 43% and 89% respectively, but the synthesis report of existing enzymatic method is less, and Yield is also lower

Method used

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  • Enzymatic synthesis method of (S)-2-aminobutanamide
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  • Enzymatic synthesis method of (S)-2-aminobutanamide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 2.1g (S)-2-aminobutyric acid methyl ester, 1.56g carbamamide and isopropanol 20mL successively in clean reactor, then add immobilized lipase 0.2g, methacrylic acid porous resin as Immobilize the material, then control the temperature and stir under the condition of 35° C., keep the temperature in a water bath for 24 hours, take a sample for HPLC analysis, and the conversion rate is greater than 95% (chromatographic column: ODS-34.6nm×250nm, UV 200nm detection; mobile phase: phosphate buffer solution (PH=2.4), acetonitrile:methanol=80:10), after the reaction, the immobilized lipase was recovered by centrifugal filtration, and the filtrate was distilled under reduced pressure The solvent was removed to obtain 1.62 g of the corresponding product (S)-2-aminobutyramide with a chiral purity of 99.5%.

Embodiment 2

[0029] Add 10.3g of (S)-2-aminobutyric acid methyl ester, 8g of ammonium carbamate and 100mL of isopropanol, 1g of immobilized lipase, and methacrylic acid porous resin as immobilization materials in a 250mL clean round bottom flask. Then control the temperature and stir under the condition of 35 ℃, keep the water bath for 24 hours, stop the reaction, take a sample for HPLC analysis, the conversion rate is greater than 95%, centrifugal filtration removes immobilized lipase for recovery, and the collected filtrate is put into another clean In the reaction flask, heat the filtrate (reaction liquid) to 80°C for about 1 hour, then add 1 g of activated carbon for decolorization treatment for 15 minutes, and after suction filtration, conduct vacuum distillation on the collected filtrate to remove the solvent, then take methanol to distill the residue The product was rinsed to remove impurities and dried to obtain 7.63 g of white solid product (S)-2-aminobutyramide, with a yield of 85...

Embodiment 3

[0031]Add 10.3g of (S)-2-aminobutyric acid methyl ester, 8g of ammonium carbamate and 100mL of tert-butanol, 1g of immobilized lipase, and methacrylic acid porous resin as immobilized materials in a 250mL clean round bottom flask. The enzyme activity can reach ≥10000PLU / g, and the particle size of the immobilized lipase is 0.5mm, then the temperature is controlled and stirred at 40°C, the reaction is kept in a water bath for 20 hours, the reaction is stopped, and samples are taken for HPLC analysis. The conversion rate is greater than 96%, centrifugal filtration to remove immobilized lipase for recovery, put the collected filtrate into another clean reaction bottle, heat the filtrate (reaction liquid) to 75°C for about 1h, then add 1.5g of activated carbon for decolorization for 15 minutes , after suction filtration, the filtrate collected was subjected to vacuum distillation to remove the solvent, then methanol was taken to rinse and remove impurities from the residue of the d...

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Abstract

The invention relates to an enzymatic synthesis method of (S)-2-aminobutylamide, and belongs to the technical field of medicine intermediate synthesis. In order to solve the problems of the existing chemical synthesis method, the invention provides the enzymatic synthesis method of the (S)-2-aminobutyramid, which comprises the following steps that in a presence of an amino donor and under the action of a catalytic amount of lipase, catalytic ammonolysis reaction is carried out on a substrate (S)-2-aminobutyric acid methyl ester to obtain a corresponding product (S)-2-aminobutyramide; and the gene sequence of the lipase is as shown in SEQ ID NO. 1. The method has high stereoselectivity and specificity, an S-type chiral configuration product is formed, the effect of high chiral purity is achieved, and the ee value of the product is high.

Description

technical field [0001] The invention relates to a method for enzymatically synthesizing (S)-2-aminobutanamide, which belongs to the technical field of pharmaceutical intermediate synthesis. Background technique [0002] Levetiracetam (Levetiracetam, LEV, trade name is Kaipu Lan) is a kind of piracetam drug developed by Belgium UCB company, the chemical name is (S)-a-ethyl-2-oxo-1- pyrrolidineacetamide. Compared with traditional drugs for the treatment of epilepsy, LEV has a new mechanism of action and can be used as an additive to treat various epilepsy in children, especially for complex partial seizures and myoclonic seizures. Compared with similar drugs, LEV has the following advantages: (1) There is a large difference between the effective dose and the toxic dose, the drug is safe, and the side effects are small; (2) The main metabolic pathway does not pass through the liver drug enzyme system, and has no interaction with other antiepileptic drugs (3) Oral absorption i...

Claims

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Application Information

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IPC IPC(8): C12P13/02
CPCC12P13/02
Inventor 杨晶晶谷绪顶程加铭陈恬张锦涛程祖福
Owner 江苏八巨药业有限公司
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