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Method for synthesizing 13C-labeled alpha-aminobutyric acid

A technology of aminobutyric acid and synthesis method, which is applied in chemical instruments and methods, carboxylate preparation, carboxylic acid amide preparation, etc., can solve the problems of inability to selectively synthesize carboxyl groups, unfavorable industrial production, and increased raw material cost, etc., and achieves good results. The effect of economy and practical application value, less by-products, and simple operation

Inactive Publication Date: 2019-05-24
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After the process is improved, the conversion rate of the reaction can be increased, but a by-product similar in nature to the product α-aminobutyric acid will be introduced, which will affect the further purification of the product, so it is not conducive to industrial production
And the biosynthesis method cannot selectively synthesize the carboxyl group 13 C markers, only all C can be carried out 13 C isotope labeling, greatly increasing the cost of raw materials

Method used

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  • Method for synthesizing 13C-labeled alpha-aminobutyric acid
  • Method for synthesizing 13C-labeled alpha-aminobutyric acid

Examples

Experimental program
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Effect test

Embodiment 1

[0031] 13 The synthetic method of C-labeled α-aminobutyric acid adopts the following method:

[0032] 5g n-butyric acid-1-( 13 COOH) was dissolved in 50ml of 1,2-dichloroethane, 6.68g of thionyl chloride was added at 0°C, and the reaction was stirred at 0°C for 6h until no HCl gas was released. The reaction liquid spins off the solvent to obtain the intermediate intermediate (1) n-butyryl chloride- 13 C 5.70g.

[0033] 5.70g intermediate (1) n-butyryl chloride- 13 Dissolve C in dichloromethane, heat to 80°C, slowly add 42.50 g of dry liquid bromine dropwise under stirring, and continue stirring for 12 hours. After the reaction, the reactant was cooled to room temperature. Spin to remove the solvent, distill under reduced pressure, collect 150 ° C light yellow oily fraction intermediate (2) 2-bromobutyric acid chloride- 13 C 8.90g.

[0034] Dissolve 33.42g of urotropine in 100ml of ethanol, stir and mix. Dry ammonia gas was introduced at room temperature until the pH of...

Embodiment 2

[0037] 13 The synthetic method of C-labeled α-aminobutyric acid adopts the following method:

[0038] 5g n-butyric acid-1-( 13 COOH) was dissolved in 50ml of dichloromethane, 20.00g of thionyl chloride was added at -20°C, and the reaction was stirred at 60°C for 8h until no HCl gas was released. The reaction liquid spins off the solvent to obtain the intermediate intermediate (1) n-butyryl chloride- 13 C 5.72g.

[0039] 5.72g intermediate (1) n-butyryl chloride- 13 Dissolve C in 1,2-dichloroethane, heat to 30°C, slowly add 8.50 g of dry liquid bromine dropwise under stirring, and continue stirring for 8 hours. After the reaction, the reactant was cooled to room temperature. Spin to remove the solvent, distill under reduced pressure, collect 150 ° C light yellow oily fraction intermediate (2) 2-bromobutyric acid chloride- 13 C 8.92g.

[0040] Dissolve 6.68g of urotropine in 100ml of methanol, stir and mix. Dry ammonia gas was introduced at room temperature until the pH ...

Embodiment 3

[0043] 13 The synthetic method of C-labeled α-aminobutyric acid adopts the following method:

[0044] 5g n-butyric acid-1-( 13 COOH) was dissolved in 50ml of benzene, 32.10g of oxalyl chloride was added at -20°C, and the reaction was stirred at 100°C for 2h until no HCl gas was released. The reaction liquid spins off the solvent to obtain the intermediate intermediate (1) n-butyryl chloride- 13 C5.74g.

[0045] 5.74g intermediate (1) n-butyryl chloride- 13 Dissolve C in chloroform, heat to 60°C, slowly add 20.50 g of dry liquid bromine dropwise under stirring, and continue stirring for 2 hours. After the reaction, the reactant was cooled to room temperature. Spin to remove the solvent, distill under reduced pressure, collect 150 ° C light yellow oily fraction intermediate (2) 2-bromobutyric acid chloride- 13 C8.91g.

[0046] Dissolve 15.50g of urotropine in 100ml of isopropanol, stir and mix. Dry ammonia gas was introduced at room temperature until the pH of the soluti...

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Abstract

The invention relates to a method for synthesizing 13C-labeled alpha-aminobutyric acid. The method comprises the steps of taking n-butyric acid-1-(13COOH) as a raw material, carrying out acylation reaction by using a chlorination reagent to obtain an intermediate n-butyryl chloride-13C, carrying out bromination reaction on the n-butyryl chloride-13C to obtain an intermediate 2-bromobutyric acid chloride-13C, and carrying out amination reaction to obtain an intermediate 2-aminobutyramide-13C; and hydrolyzing to obtain alpha-aminobutyric acid-(13COOH) as a colorless solid. Compared with the prior art, the method has the advantages that the reaction process is simple, an aftertreatment process is simple and convenient, and the like. The total reaction yield is more than or equal to 72% (basedon butyric acid-1-(13COOH)), the chemical purity is more than or equal to 99%, and the isotopic abundance is more than or equal to 98 atom% 13C.

Description

technical field [0001] The present invention relates to the preparation method of the organic compound of stable isotope label, especially relates to a kind of 13 C stable isotope labeled α-aminobutyric acid-( 13 COOH) organic synthesis method. Background technique [0002] As a unique emerging science, stable isotopes and their labeled compounds have been applied in almost all high-tech fields, especially in the field of modern medical diagnosis applications. α-aminobutyric acid is a natural amino acid that inhibits the transmission of human nerve information. It is an important chemical raw material and pharmaceutical intermediate. It has become an important chiral intermediate for many chiral drugs and is widely used in drug synthesis, such as α-aminobutyric acid Acid is the main raw material for the synthesis of the new antiepileptic drug levetiracetam, and also the key chiral precursor for the synthesis of the antibacterial and anti-tuberculosis drug ethambutol hydroc...

Claims

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Application Information

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IPC IPC(8): C07C51/60C07C53/42C07C51/62C07C53/50C07C231/02C07C237/06C07C227/18C07C229/08
Inventor 徐建飞王伟刘占峰雷雯侯捷
Owner SHANGHAI RES INST OF CHEM IND
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