7324-11-0

Usage

Uses

Used in Pharmaceutical Industry:
L-2-Aminobutanamide is used as a building block for the synthesis of complex molecules and pharmaceutical intermediates, contributing to drug discovery and medicinal research. Its role in creating new pharmaceutical compounds is crucial for advancing treatments and therapies.
Used in Organic Chemistry:
L-2-Aminobutanamide is used as a fundamental raw material in organic chemistry, enabling the development of various organic compounds and contributing to the broader field of chemical research and synthesis.

Upstream product

• 2835-81-6 2-aminobutanoic acid 
• 53726-14-0 DL-2-aminobutanamide 
• 5959-29-5 S-(+)-2-amino-n-butyric acid hydrochloride 
• 7682-18-0 (S)-2-aminobutyric acid methyl ester hydrochloride 
• 53726-14-0 (S)-2-amino-butanamide hydrochloride 
• 4510-08-1 L-methioninamide 
• 2483-62-7 (S)-2-aminobutyric acid methyl ester 
• 40651-89-6 2-aminobutyronitrile 

Downstream Products

• 102767-28-2 levetiracetam 
• 357336-20-0 brivaracetam 
• 357336-99-3 ((2S)-2-[(4S)-2-oxo-4-propyltetrahydro-1H-pyrrol-1-yl]butanamide) 
• 53726-14-0 (S)-2-amino-butanamide hydrochloride 
• 2483-62-7 (S)-2-aminobutyric acid methyl ester 
• 1076190-33-4 methyl 4-{[(1S)-1-(aminocarbonyl)propyl]amino}-3-phenylbutanoate 
• 1076190-08-3 (2S)-2-{[(benzylamino)acetyl]amino}butanamide 
• 357338-13-7 (2S)-4,5-dehydro-(2-oxo-4-n-propyl-1-pyrrolidinyl)-2-butanamide 
• 102767-31-7 (S)-2-(4-chlorobutyramido)butanamide 

Relevant academic research and scientific papers

Method for splitting aminobutanamide by using ammonium hydrogen tartrate

The present invention relates to the technical field of aminobutanamide resolution, and discloses a method for resolving aminobutanamide by using ammonium hydrogen tartrate, and the method comprises the following steps: taking 10-20 parts of ammonium tartrate, placing ammonium tartrate in a reaction flask, adding 20-40 parts of purified water, and performing stirring for 0.5-1.5 h to obtain an ammonium tartrate solution. According to the method for resolving aminobutanamide by using ammonium hydrogen tartrate, the ammonium hydrogen tartrate is used as a reactant and is subjected to resolution reaction with racemic 2-aminobutanamide, and an L-2-aminobutanamide ammonium hydrogen tartrate wet product obtained after the reaction is reacted with methanol and ammonia gas, so L-2-aminobutanamide and ammonium hydrogen tartrate can be separated out; the L-2-aminobutanamide liquid can be obtained, the ammonium hydrogen tartrate can be converted into the ammonium tartrate solid for recovery and storage, and the L-2-aminobutanamide solid can be used for splitting the aminobutanamide in the next ammonium hydrogen tartrate preparation so as to achieve the recovery and reutilization of the reactants, such that the production cost is reduced, and the low cost purpose is achieved.

Continuous-flow protocol for the synthesis of enantiomerically pure intermediates of anti epilepsy and anti tuberculosis active pharmaceutical ingredients

Continuous-flow production of chiral intermediates plays an important role in the development of building blocks for Active Pharmaceutical Ingredients (APIs), being α-amino acids and their derivatives widely applied as building blocks. In this work we developed two different strategies for the synthesis of intermediates used on the synthesis of levetiracetam/brivaracetam and ethambutol. The results obtained show that methionine methyl ester can be continuously converted to the desired ethambutol intermediate by RANEY Nickel dessulfurization/reduction strategy whereas levetiracetam/brivaracetam intermediates could be synthesized by both RANEY Nickel (without H2) and Pd/C-H2 approach or by photochemical desulfurization.

PROCESS FOR PREPARING BRIVARACETAM

The present invention relates to a new process for preparing brivaracetam. (Ib)

Processing technique of L-2-amino butyramide hydrochloride

The invention relates to a processing technique of L-2-amino butyramide hydrochloride. The processing technique includes: using 2-chlorobutyric acid as a raw material and hexamethylenetetramine as a catalyst to prepare 2-aminobutyric acid; using L-tartaric acid to resolve 2-aminobutyric acid to obtain L-2-aminobutyric acid, acrylating L-2-aminobutyric acid to obtain L-2-aminobutyryl compound, and obtaining L-2-amino butyramide hydrochloride under the condition of ammonia water. The processing technique has the advantages that by the processing technique, reaction yield is increased, and byproducts are few. In addition, the processing technique is mild in reaction condition, easy in reaction control, low in cost, high in yield, high in product purity, low in equipment requirement and suitable for industrial production, and technique safety is improved greatly.

Preparation method for levetiracetam intermediate L-2-aminobutanamide hydrochloride

The invention relates to a preparation method for a levetiracetam intermediate L-2-aminobutanamide hydrochloride. The method comprises the steps that n-propanal reacts with ammonia and hydrocyanic acid in a water solution under existing of ammonium chloride to prepare 2-amidogen butyronitrile, a certain amount of liquid ammonia and hydrocyanic acid are fed into mother liquor, and the mother liquor can be used indiscriminately for infinite times; the 2-amidogen butyronitrile is hydrolyzed in a 1% sodium hydroxide water solution to obtain 2-aminobutanamide, and water can be used indiscriminately for infinite times after being distilled; the 2-aminobutanamide is subjected to resolution to obtain L-2-aminobutanamide; salifying is carried out, and the L-2-aminobutanamide hydrochloride is obtained. The method has the advantages that the product quality is good, no waste water is produced in the production process, and the cost is low, and the preparation method is suitable for industrial production.

Preparation method of S-2-aminobutanamide

The invention provides a preparation method of S-2-aminobutanamide, comprising the steps of 1), reacting hydrogen cyanide, ammonia and n-propanal as materials to obtain 2-aminobutanenitrile; 2), separating a reacted liquid of step 1) by means of extraction to obtain an oil phase and a water phase, adding a catalyst and an alkali solution into the oil phase to carrying out hydrolysis, and reacting to obtain hydrolysate; 3), adding an acid or acid aqueous solution into the hydrolysate of step 2), separating to obtain an oil phase and a water phase, and separating the water phase to obtain S-2-aminobutanamide. The hydrogen cyanide, n-propanal and ammonia are reacted as materials to synthesize 2-aminobutanenitrile, the 2-aminobutanenitrile is hydrolyzed to directly obtain a target product, little byproducts are produced in reaction, and the content of the target product is high; little waste water and waste gas are produced in reaction, zero residue is produced, and there is no mass waste salts produced in the sodium cyanide process; the operation is simple, and product yield and purity are high.

An asymmetric synthesis of Levetiracetam

An asymmetric synthesis of (S)-levetiracetam has been developed through application of a Strecker reaction using [(1S)- 1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of propanaldehyde to a solution of sodium cyanide and [(1S)-1-(4-methoxyphenyl)ethyl]amine hydrochloride in the mixture of methanol and water at 25-30°C afforded diastereomerically pure 2-[2-(4-methoxyphenyl)-(S)-methylethyl-amino]-( S )-butyronitrile hydrochloride compound 4 . In this reaction cyanide group attack at less hindered side that is re-face of the imine intermediate gave the diastereomerically pure nitrile 4. Which upon hydrolysis in the presence of 6 M aqueous hydrochloride solution obtained enantiomerically pure (S )-2- aminobutyric acid hydrochloride 5, is a key intermediate for the (S)-levetiracetam. This intermediate further react with SOCl2 in presence of methanol formed S-2-amino methyl butyrate as in situ intermediate which on further ammonalysis in the presence of methnaolic ammonia as a solvent under ammonia pressure provided S-2-amino butyramide hydrochloride 6 which further condensed with 4-chlorobutyryl chloride 7 and followed by cyclization in the presence of potassium hydroxide, dichloromethane solvent used catalytic amount of tetra butyl ammonium bromide afforded crude (S)-levetiracetam 1, further recrystalization in the presence of ethyl acetate obtained pure (S)-levetiracetam 1.

Synthesis of tritium-labeled levetiracetam ((2S)-2-(2-oxopyrrolidin-1-yl) butanamide) with high specific activity

A method for the preparation of [A3H]levetiracetam with a high specific activity of 98Ci/mmol (3.6TBq/mmol) is described. The radioligand proved to be highly useful for the labeling of specific levetiracetam binding sites in rat brain membrane preparations.

PROCESS FOR PREPARING 2-OXO-1-PYRROLIDINE DERIVATIVES

The present invention relates to a new process for preparing 2-oxo- I -pyrrolidine derivatives of general formula (I) wherein the substituents are as defined in the specification.

PROCESS FOR PREPARING 2-OXO-1-PYRROLIDINE DERIVATIVES BY INTRAMOLECULAR ALLYLATION

The present invention relates to a new process for preparing 2-oxo-1-pyrrolidine derivatives of general formula (I), comprising the cyclisation of an intermediate of general formula (II) wherein the substituents are as defined in the specification.