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Method for preparing (S)-2-aminobutanamide hydrochloride

A technology of aminobutyramide and hydrochloride, which is applied in the field of preparation of levetiracetam intermediates, can solve the problems of potential safety hazards, high temperature and pressure, and high cost of desalination, and can avoid chiral separation, process The effect of controllable stability enhancement and avoiding a large number of outgassing reactions

Active Publication Date: 2014-09-24
CANGZHOU SENARY CHEM SCI TEC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The prior art generally adopts the hydantoin method to prepare this important intermediate, but this method has technical defects such as high temperature and pressure when hydantoin is hydrolyzed, which has potential safety hazards, and releases a large amount of ammonia gas, and high cost of desalination. question

Method used

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  • Method for preparing (S)-2-aminobutanamide hydrochloride
  • Method for preparing (S)-2-aminobutanamide hydrochloride
  • Method for preparing (S)-2-aminobutanamide hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A preparation method of (S)-2-aminobutyramide hydrochloride, comprising the following steps: (1) using n-propionaldehyde as raw material to react with sodium bisulfite, potassium cyanide and R-phenylglycinol to obtain normal Intermediate 1;

[0033] The ingredient ratio is:

[0034] Product name Dosage (g) Specification Remarks

[0035] Potassium cyanide 385 30%

[0036] R-Phenylglycine 236 Industrial

[0037] Sodium bisulfite 200 Industrial

[0038] Propionaldehyde 100 Industrial

[0039] Ethyl acetate 600 Industrial Recyclable1

[0040] Petroleum ether 600 Industrial

[0041] The specific operation steps are: add 385g of potassium cyanide with a mass fraction of 30% and 100g of n-propanal in a 2L three-necked flask, add 200g of sodium bisulfite after stirring, stir to dissolve, cool in a water bath, and dropwise add 236g of R-phenylglycinol aqueous solution was dropped within about 1 hour, then stirred at 70-80°C for 6 hours, and the propionaldehyde basically d...

Embodiment 2

[0059] A preparation method of (S)-2-aminobutanamide hydrochloride, comprising the following steps: (1) reacting n-propanal, sodium bisulfite, potassium cyanide and R-phenylglycinol as raw materials to prepare Intermediate 1; the mass ratio of n-propionaldehyde, sodium bisulfite, potassium cyanide and R-phenylglycinol is 1:1:1.1:1.1, and the reaction temperature is 40°C;

[0060] The structural formula of intermediate 1 is:

[0061]

[0062] The reaction equation is:

[0063] ;

[0064] (2) Hydrolysis: add sodium hydroxide solution to intermediate 1, and hydrolyze to obtain intermediate 2; the mass fraction of sodium hydroxide solution is 30%, and the amount of sodium hydroxide added is 1 g of sodium hydroxide per gram of n-propionaldehyde solution, the reaction temperature is 100°C;

[0065] The structural formula of intermediate 2 is:

[0066]

[0067] The reaction equation is:

[0068] ;

[0069] (3) Hydrogenation reaction: add a catalyst, and hydrogenate the ...

Embodiment 3

[0073] A preparation method of (S)-2-aminobutanamide hydrochloride, comprising the following steps: (1) reacting n-propanal, sodium bisulfite, potassium cyanide and R-phenylglycinol as raw materials to prepare Intermediate 1; the mass ratio of n-propionaldehyde, sodium bisulfite, potassium cyanide and R-phenylglycinol is 1:1.5:1:1.5, and the reaction temperature is 50°C;

[0074] The structural formula of intermediate 1 is:

[0075]

[0076] The reaction equation is:

[0077] ;

[0078] (2) Hydrolysis: add sodium hydroxide solution to intermediate 1, and hydrolyze to obtain intermediate 2; the mass fraction of sodium hydroxide solution is 30%, and the amount of sodium hydroxide added is 1.5g of hydroxide per gram of n-propionaldehyde Sodium solution, the reaction temperature is 120°C;

[0079] The structural formula of intermediate 2 is:

[0080]

[0081] The reaction equation is:

[0082] ;

[0083] (3) Hydrogenation reaction: add a catalyst, and hydrogenate t...

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Abstract

The invention discloses a method for preparing (S)-2-aminobutanamide hydrochloride. The method comprises the following steps: (1) carrying out reactions by taking n-propanal, sodium hydrogen sulfite, editpotassium cyanide and R-phenylglycinol as raw materials so as to prepare an intermediate 1; (2) hydrolyzing, namely adding a sodium hydroxide solution into the intermediate 1, and hydrolyzing to obtain an intermediate 2; (3) hydrogenation, namely adding a catalyst, performing hydrogenation on the generated intermediate 2 to obtain the 2-aminobutanamide hydrochloride under acidic conditions. According to the method, the reaction process is performed under approximately neutral conditions, and lots of air bleeding reactions are avoided, so that the controlled stability in the process is greatly improved, chiral resolution is avoided, qualified chiral products can be synthesized through one-time induction, and thus a beneficial process is provided for industrial production of an important intermediate 2-aminobutanamide hydrochloride.

Description

technical field [0001] The invention belongs to the technical field of acyclic or carbocyclic compounds, and relates to a preparation method of a levetiracetam intermediate. Background technique [0002] The chemical name of levetiracetam is: (S)-alpha-ethyl-2-oxo-1-acetamide pyrrolidine, and the structural formula is as follows: [0003] [0004] (S)-2-Aminobutanamide is an important intermediate of the antiepileptic drug levetiracetam (Levet iracetam is a pyrrolidone derivative). FDA approved, marketed in the United States. It is currently the only drug used to treat localized and secondary generalized epilepsy. It has two properties of anti-epileptic and anti-epileptic, and can prevent the occurrence of epilepsy. As a new generation of epilepsy drug, levetiracetam has better anti-epileptic efficacy and better tolerance, fewer drug interactions, lower incidence of adverse reactions, close to 100% oral bioavailability, and high treatment safety index. advantage. It ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/06C07C231/12C07C255/24C07C253/00
Inventor 张少平郭志雄王平刘劲松张月成张伟焦兴斌黄培晨佟建强
Owner CANGZHOU SENARY CHEM SCI TEC
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