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Preparation method of 2-amino-2-phenylbutyric acid

A technology of phenylbutyric acid and amino, which is applied in the field of preparation of trimebutine pharmaceutical intermediate 2-amino-2-phenylbutyric acid, can solve problems affecting product quality and yield, and achieve high atom economy Effect

Pending Publication Date: 2022-06-21
抚顺顺能化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Studies have found that in the process of preparing different kinds of α-amino acids by this method, different ammonia sources and cyanide sources are selected, and the reaction mechanism is different, and different intermediates (α-aminonitrile and hydantoin) will be obtained. Affect product quality and yield

Method used

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  • Preparation method of 2-amino-2-phenylbutyric acid
  • Preparation method of 2-amino-2-phenylbutyric acid

Examples

Experimental program
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Effect test

Embodiment 1

[0038] 134g (1.0mol) of propiophenone, 245g (1.5mol) of 30% sodium cyanide solution, 192.16g (2.0mol) of ammonium carbonate and 6.7g of tetrabutylammonium bromide were added to a 2000mL there-necked flask, and then added 200g deionized water, stir to dissolve. The reaction solution was slowly heated to 65-70° C. and incubated for 15 hours. After the reaction was completed, suction filtration was performed, and the filter cake was washed with deionized water to obtain a wet product of 5-ethyl-5-phenylhydantoin.

[0039] After stirring and dissolving 5-ethyl-5-phenylhydantoin wet product, 120g (3.0mol) solid sodium hydroxide and 1000g deionized water, transfer to the autoclave, slowly heat up to 180°C, and heat preservation reaction 6h. After the reaction, the temperature was lowered to room temperature, the material was transferred to a 2000 mL flask, and hydrochloric acid was added dropwise to adjust pH=5.5-6.0. The material was extracted, the filter cake was washed with dei...

Embodiment 2

[0041] 134g (1.0mol) of propiophenone, 294g (1.8mol) of 30% sodium cyanide solution, 288.24g (3.0mol) of ammonium carbonate and 6.7g of benzyltriethylammonium chloride were added to the there-necked flask of 2000mL, Add 300 g of deionized water and stir to dissolve. The reaction solution was slowly heated to 75-80° C. and incubated for 10 hours. After the reaction was completed, suction filtration was performed, and the filter cake was washed with deionized water to obtain a wet product of 5-ethyl-5-phenylhydantoin.

[0042] The above-mentioned 5-ethyl-5-phenylhydantoin wet product, 120g (3.0mol) solid sodium hydroxide and 1000g deionized water were stirred and dissolved and then transferred to the autoclave, slowly warming up to 180° C. Reaction 6h. After the reaction, the temperature was lowered to room temperature, the material was transferred to a 2000 mL flask, and 50% sulfuric acid was added dropwise to adjust pH=5.5-6.0. The material was extracted, the filter cake was...

Embodiment 3

[0044] 134g (1.0mol) of propiophenone, 294g (1.8mol) of 30% sodium cyanide solution, 480.4g (5.0mol) of ammonium carbonate and 13.4g of tetrabutylammonium bromide were added to a 2000mL there-necked flask, and then added 500g deionized water, stir to dissolve. The reaction solution was slowly heated to 65-70° C. and incubated for 15 hours. After the reaction was completed, suction filtration was performed, and the filter cake was washed with deionized water to obtain a wet product of 5-ethyl-5-phenylhydantoin.

[0045]The above-mentioned 5-ethyl-5-phenylhydantoin wet product, 120g (3.0mol) solid sodium hydroxide and 1000g deionized water were stirred and dissolved, and then transferred to the autoclave, slowly warming up to 160 ° C, insulation The reaction was carried out for 8 hours. After the reaction, the temperature was lowered to room temperature, the material was transferred to a 1000 mL flask, and 50% sulfuric acid was added dropwise to adjust pH=5.5-6.0. The material...

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Abstract

The invention discloses a preparation method of 2-amino-2-phenylbutyric acid, which comprises the following steps: mixing propiophenone, sodium cyanide, ammonium carbonate and a phase transfer catalyst, dissolving in water, carrying out cyclization reaction, filtering, and washing to obtain an intermediate 5-ethyl-5-phenyl hydantoin; the preparation method comprises the following steps: adding 5-ethyl-5-phenyl hydantoin into a sodium hydroxide solution, carrying out hydrolysis reaction under the conditions of high temperature and high pressure, adjusting the pH value by using acid after the hydrolysis reaction is finished, filtering, washing and drying to obtain a final product. On the basis of alpha-amino acid synthesized by a traditional Strecker method, ammonium carbonate is taken as an ammonia source, sodium cyanide is taken as a cyanogen source, and a phase transfer catalyst is added, so that the preparation method of 2-amino-2-phenylbutyric acid, which is simple, feasible, green, environment-friendly and suitable for large-scale industrial production, is obtained. The HPLC (High Performance Liquid Chromatography) purity of the prepared product is greater than 99%, and the yield can reach more than 80% on the basis of the raw material propiophenone.

Description

technical field [0001] The invention relates to the field of medicinal chemical synthesis, in particular to a preparation method of trimebutine medicinal intermediate 2-amino-2-phenylbutyric acid. Background technique [0002] 2-Amino-2-phenylbutyric acid belongs to the α-amino acid compound and is the key intermediate in the synthesis of trimebutine. Trimebutine maleate is a new type of gastric function regulator with a unique bidirectional regulating function, which can directly act on smooth muscle and regulate gastrointestinal motility. It can enhance the function of the digestive system when its function is low, inhibit its function when the digestive system is hyperactive, and can also be used clinically to treat and improve abdominal fullness, nausea, belching, abdominal pain caused by chronic gastritis, gastric ulcer, etc. And abnormal laxative caused by irritable bowel syndrome, side effects are small. [0003] α-amino acid compounds can usually be synthesized by ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/24C07C229/36C07D233/74
CPCC07C227/24C07D233/74C07C229/36
Inventor 周怡李昊胡成楠
Owner 抚顺顺能化工有限公司
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