Unlock instant, AI-driven research and patent intelligence for your innovation.

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, so as to avoid chiral resolution and process The effect of controllable stability enhancement and avoiding a large amount of outgassing reaction

Active Publication Date: 2014-03-12
CANGZHOU SENARY CHEM SCI TEC
View PDF3 Cites 3 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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 method for preparing (S)-2-aminobutanamide hydrochloride, including the following steps: (1) Using n-propionaldehyde as a raw material, reacting with sodium bisulfite, potassium cyanide, and R-phenylglycinol to obtain Intermediate 1;

[0033] The ingredient ratio is:

[0034] Product name Dosage (g) Specification Remarks

[0035] Potassium cyanide 385 30%

[0036] R-Phenylglycinol 236 Industry

[0037] Sodium bisulfite 200 industrial

[0038] Propionaldehyde 100 industry

[0039] Ethyl acetate 600 Industrial recyclable 1

[0040] Petroleum ether 600 industry

[0041] The specific operation steps are: add 385 g of 30% potassium cyanide and 100 g of n-propanal into a 2L three-necked flask, add 200 g of sodium bisulfite after stirring, stir to dissolve, cool in a water bath, and add dropwise at 0-25°C 236g R-phenylglycinol aqueous solution, drip in about 1 hour, then stir at 70~80℃ for 6 hours, gas phase detection of propionaldehyde basically disappeared, and then extracted with eth...

Embodiment 2

[0059] A method for preparing (S)-2-aminobutanamide hydrochloride, including the following steps: (1) Prepared by reacting n-propionaldehyde, sodium bisulfite, potassium cyanide and R-phenylglycinol as raw materials 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 1g sodium hydroxide per gram of n-propanal Solution, the reaction temperature is 100℃;

[0065] The structural formula of Intermediate 2 is:

[0066]

[0067] The reaction equation is:

[0068] ;

[0069] (3) Hydrogenation reaction: Add a catalyst, hydrogenate the produced intermediate 2 under aci...

Embodiment 3

[0073] A method for preparing (S)-2-aminobutanamide hydrochloride, including the following steps: (1) Prepared by reacting n-propionaldehyde, sodium bisulfite, potassium cyanide and R-phenylglycinol as raw materials 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-propanal. Sodium solution, the reaction temperature is 120℃;

[0079] The structural formula of Intermediate 2 is:

[0080]

[0081] The reaction equation is:

[0082] ;

[0083] (3) Hydrogenation reaction: Add catalyst, hydrogenate the produced intermediate 2 under...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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 levetiracetam intermediates. Background technique [0002] The chemical name of Levetiracetam is (S)-alpha-ethyl-2oxo-1-acetamide pyrrolidine, and the structural formula is as follows: [0003] [0004] (S)-2-Aminobutanamide is an important intermediate of the antiepileptic drug Levet iracetam (Levet iracetam is a pyrrolidone derivative). Levet iracetam was researched and developed by the Belgian UCB company and obtained in April 2000. Approved by the FDA and listed in the United States. It is currently the only medicine used to treat localized and secondary generalized epilepsy. It has anti-epileptic and anti-epileptic properties and can prevent the occurrence of epilepsy. As a new generation of epilepsy drug, Levetiracetam has better anti-epileptic efficacy and good tolerance, less drug interaction, lower incidence of adverse reactions...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com