52950-37-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-Amino-3-phenylbutanoic acid hydrochloride is used as a pharmaceutical intermediate for the synthesis of various medications, leveraging its ability to be a building block in the creation of new therapeutic agents.
Used in Neurological Treatments:
In the field of neurology, (S)-4-Amino-3-phenylbutanoic acid hydrochloride is used as a potential therapeutic agent for the treatment of anxiety and other neurological disorders, due to its capacity to interact with neurological pathways and potentially alleviate symptoms.

Upstream product

• 78533-73-0 3-phenylglutaronitrile 
• 34687-03-1 4-nitro-3-phenylbutanoic acid methyl ester 
• 1431854-83-9 C₁₂H₁₇NO₂ 
• 1217022-86-0 (3S, 4R)-(-)-4-phenyl-3-carbethoxy-2-pyrrolidinone 
• 84872-79-7 4-amino-3-phenylbutanoic acid methyl ester 
• 62384-61-6 α-phenyl-β-benzoyl-γ-nitrobutyrate ethyl ester 
• 1198-97-6 4-phenylpyrrolidin-2-one 

Downstream Products

• 71657-88-0 (4R)-4-phenyl-2-pyrrolidone 
• 120438-10-0 C₁₅H₂₁NO₃Si 
• 70291-40-6 2-oxo-4-phenyl-1-pyrrolidineacetic acid, ethyl ester 
• 67118-34-7 2-(2-oxo-4-phenylpyrrolidin-1-yl)acetic acid 
• 68497-63-2 methyl-2-oxo-4-phenylpyrrolidine-1-acetate 
• 106869-48-1 4-phenyl-1-(trimethylsilyl)-2-pyrrolidinone 

Relevant academic research and scientific papers

Divergent Synthesis of γ-Amino Acid and γ-Lactam Derivatives from meso-Glutaric Anhydrides

The first divergent synthesis of both γ-amino acid and γ-lactam derivatives from meso-glutaric anhydrides is described. The organocatalytic desymmetrisation with TMSN3 relies on controlled generation of a nucleophilic ammonium azide species mediated by a polystyrene-bound base to promote efficient silylazidation. After Curtius rearrangement of the acyl azide intermediate to access the corresponding isocyanate, hydrolysis/alcoholysis provided uniformly high yields of γ-amino acids and their N-protected counterparts. The same intermediates were shown to undergo an unprecedented decarboxylation–cyclisation cascade in situ to provide synthetically useful yields of γ-lactam derivatives without using any further activating agents. Mechanistic insights invoke the intermediacy of an unconventional γ-N-carboxyanhydride (γ-NCA) in the latter process. Among the examples prepared using this transformation are 8 APIs/molecules of considerable medicinal interest.

Assembling of medium/long chain-based β-arylated unnatural amino acid derivatives via the Pd(II)-catalyzed sp3 β-C-H arylation and a short route for rolipram-type derivatives

In this paper, we report the assembling of libraries of β-arylated short/medium/long chain-based non-α-amino acid (aminoalkanoic acid) derivatives via the Pd(II)-catalyzed, bidentate directing group 8-aminoquinoline-aided sp3 β-C-H activation/arylation method. Short/medium chain-based unnatural amino acid derivatives containing an aryl group at the β-position are promising small molecules with therapeutic properties. Thus, it is necessary to enrich the libraries of short/medium/long chain-based unnatural amino acid derivatives containing an aryl group at the β-position. Considering the importance of β-arylated short/medium/long chain-based non-α-amino acid derivatives, an inclusive attention was paid to explore the Pd(II)-catalyzed sp3 β-C-H arylation of short/medium/long chain-based non-α-amino acids. Representative synthetic transformations including a short route for the assembling of rolipram and related compounds and 3-arylated GABA derivatives such as, baclofen, phenibut and tolibut were shown using selected β-C-H arylated non-α-amino acid derivatives.

COMPOUND, MANUFACTURING METHOD OF COMPOUND THROUGH ASYMMETRIC MICHAEL ADDITION USING THE COMPOUND AND MANUFACTURING METHOD OF PHENIBUT USING THE COMPOUND

The present invention relates to a compound, a method of producing compounds through an asymmetric Michael addition reaction by using the same, and a method of producing a phenibut compound. Specifically, the compound of the present invention is represented by chemical formula 1. In the chemical formula 1: L represents #AAA# or #BBB# (wherein X represents sulfur or oxygen); R_1 represents hydrogen, an alkyl group having 1-5 carbons, an aryl group having 6-12 carbon atoms, or a benzyl group; R_2 represents an aryl group having 6-12 carbon atoms; R_3 represents hydrogen or an aryl group having 1-12 carbon atoms; and hydrogen in R_1, R_2, and R_3 may be each independently substituted by an alkyl group having 1-5 carbon atoms.COPYRIGHT KIPO 2018

A novel method for the synthesis of racemic pregabalin, baclofen and 3-phenibut involving lossen rearrangement

Pregabalin,baclofen,and3-phenibutareγ-aminobutyricacid receptorsusedasanticonvulsant agents. The racemic forms of these anticonvulsants have been prepared by Lossen rearrangement. This procedure also provides an easy method to prepare carbamates useful intermediates to prepare anticonvulsants. This process is economical and easy to scale-up and yields are good.

Synthesis of Nonracemic Tetrazole GABA Analogs

Nonracemic 3-substituted 4-(1H-tetrazol-1-yl)butanoic acids, analogs of the neurotropic drugs phenibut, tolibut, and baclofen, were synthesized by a three-component reaction of the R-isomers of the corresponding amino acids, triethyl orthoformate, and sod

A process for preparing 3 - phenyl - 4 - aminobutyric acid hydrochloride process (by machine translation)

The present invention provides a process for preparing 3 - phenyl - 4 - aminobutyric acid hydrochloride of the process, the use of cinnamic acid methyl ester and nitromethane as the reaction substrate, nitromethane can be used as the reaction substrate bu

Method for synthesizing 4-amino-3-phenylbutyric acid hydrochloride

The invention provides a method for synthesizing 4-amino-3-phenylbutyric acid hydrochloride. The synthetic method comprises the following steps: preparing methyl 4-nitro-3-phenyl butyrate, preparing methyl 4-amino-3-phenyl butyrate, and treating to obtain the product. According to the synthetic method disclosed by the invention, a complete process for synthesizing 4-amino-3-phenylbutyric acid hydrochloride is created, the synthetic method is simple in process, high in yield and low in cost, and the main problems that the initial raw materials used in the conventional process are high in price, the operation steps are onerous and pollution in the production process is severe are solved.

New multicomponent reaction for the direct synthesis of β-aryl-γ-nitroesters promoted by hydrotalcite-derived mixed oxides as heterogeneous catalyst

A new approach based on multicomponent/domino combined reactions for the synthesis of γ-nitroesters promoted by a mixed aluminium-magnesium oxides derived from hydrotalcite-like material was developed. Different γ-nitroesters were synthesized in 15-95percent yield using Meldrum's acid, aromatic aldehydes, nitromethane and different alcohols as reagents and solvents. The γ-aminobutyric acid derivatives, Phenibut and Baclofen, were prepared in 63 and 61percent overall yield, respectively, through a two steps synthetic strategy. A mechanistic pathway was proposed based on the gas chromatography mass spectrometry (GC-MS) and electrospray ionization mass spectrometry (ESI-MS) experiments.

L -Proline Derived Bifunctional Organocatalysts: Enantioselective Michael Addition of Dithiomalonates to trans-β-Nitroolefins

A series of novel l-proline derived tertiary amine bifunctional organocatalysts 9 are reported, which were applied to the asymmetric Michael addition of dithiomalonates 2 to trans-β-nitroolefins 1. The reaction proceeded in high yields (up to 99%) with high enantioselectivities (up to 97% ee). The synthetic utility of this methodology was demonstrated in the short synthesis of (R)-phenibut in high yield.

A 4-amino-3-phenyl-butyric acid hydrochloride method for the synthesis of

A provided synthetic method for 4-amino-3-phenylbutyric acid hydrochloride comprises the steps: preparing ethyl benzoylacetate, preparing nitroethenylbenzene, preparing an addition product, and processing to obtain the product. The synthetic method is an integral technology for synthesizing 4-amino-3-phenylbutyric acid hydrochloride. The method is simple in technology, high in yield and relatively low in cost, and mainly solves the problems that an initial raw material used in the prior art is high in price, operation steps are tedious and a production process is large in pollution.