1204818-19-8

Basic information

• Product Name: (R)-3-AMino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride
• Synonyms: Sitagliptin Impurity 8;(R)-b-Amino-2,4,5-trifluoro-benzenebutanoic acid HCl;Sitagliptin Impurity 17
• CAS NO: 1204818-19-8
• Molecular Formula: C₁₀H₁₀F₃NO₂*ClH
• Molecular Weight: 269.6480496
• Mol File: 1204818-19-8.mol

Chemical Properties

• Melting Point: 218-220℃
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive: Air Sensitive
• CAS DataBase Reference: (R)-3-AMino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-AMino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride(1204818-19-8)
• EPA Substance Registry System: (R)-3-AMino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride(1204818-19-8)

Safety Data

• Hazardous Substances Data: 1204818-19-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Amino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable component in the development of new drugs and medications.
Used in Research and Development:
3-ATPB is employed as a research compound in the field of medicinal chemistry, where it is used to study the interactions of different molecules and their potential applications in drug discovery. Its specific properties allow researchers to explore new avenues in the development of therapeutic agents.
Used in Drug Synthesis:
(R)-3-Amino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride is used as a key building block in the synthesis of complex drug molecules. Its presence in the molecular structure can influence the pharmacological properties of the final product, making it an essential component in the creation of novel therapeutic agents.
Used in Quality Control and Analysis:
3-ATPB is utilized as a reference compound in the quality control and analysis of pharmaceutical products. Its well-defined properties and characteristics make it a reliable standard for comparing the purity and effectiveness of other compounds in the pharmaceutical industry.

Upstream product

• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 1234321-83-5 (R)-methyl-3-N-acetylamino-4-(2,4,5-trifluorophenyl)butanoate 
• 1374966-98-9 (S)-3-(((benzyloxy)carbonyl)amino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoicacid 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 1152439-74-1 (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 1151240-91-3 (3R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 1204818-17-6 (R)-β-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester di-p-toluoyl-D-tartaric acid salt 
• 1151240-88-8 3-oxo-4-(2,4,5-trifluorophenyl)-butyric acid ethyl ester 
• 1151240-92-4 ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate 
• 1152439-73-0 2,2-dimethyl-5-[2-(2,4,5-trifluorophenyl)acetyl]-[1,3]dioxane-4,6-dione 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 

Downstream Products

• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 

Relevant articles and documents

Manufacturing process for sitagliptin from L-aspartic acid

The present invention relates to a novel manufacturing process of pharmaceutically active compound of formula I used as oral anti-diabetic drug. Starting from L-aspartic acid derivate of formula IV the invention describes preparation of the chiral (R)-β-amino acid of formula II known as a precursor in the synthesis of Sitagliptin (formula I).

PROCESS FOR PREPARING R-BETA-AMINO PHENYLBUTYRIC ACID DERIVATIVES

Disclosed is a process for preparing single enantiomers of beta-amino phenylbutyric acid derivatives and pharmaceutically acceptable salts thereof, which affords the desired compounds having special optical configuration. The process comprises a step of chemical synthesis and a step of resolving the optical isomers of beta-amino phenylbutyric acid derivatives with a resolving agent. The resolving step comprises reacting the optical isomers with resolving agents, such as di-para-toluoyl-L-tartaric acid and di-para-toluoyl-D-tartaric acid. The obtained R-beta-amino phenylbutyric acid derivatives (I) have high optical purity, and the total yield of the accumulative resolution of the laevo and the dextro isomer is up to above 70%.

A PROCESS FOR PREPARING R-BETA-AMINO PHENYLBUTYRIC ACID DERIVATIVES

Disclosed is a process for preparing chiral pharmaceutical intermediates of R-beta-amino phenylbutyric acid derivatives (I) and pharmaceutically acceptable salts thereof, which affords the desired object compounds having special optical configuration by chemosynthesis process comprising resolving the optical isomer mixtures of beta-amino phenylbutyric acid derivatives with resolving agent. This process comprises the resolving step of salification in alcoholic solvent or aquesous solution of alcohol with resolving agent of di-para-toluoyl-L-tartaric acid and di-para-toluoyl-D-tartaric acid. The obtained R-beta-amino phenylbutyric acid derivatives (I) have high optical purity, and the total yield of the accumulative resolution of the laevo and the dextro isomer is up to above 70%. The R-beta-amino phenylbutyric acid derivatives (I) produced by this process can be better used in synthesizing medicament.

Improved enzymatic syntheses of valuable β-arylalkyl-β-amino acid enantiomers

The enantioselective (E～ 200) Burkholderia cepacia-catalysed hydrolyses of β-amino esters with H2O (0.5 equiv.) in t-BuOMe or in i-Pr2O at 45 °C are described. The enantiomers of biologically relevant β-arylalkyl-substituted β-amino acids, and especially (R)-3-amino-3-(2,4,5-trifluorophenyl)butanoic acid, the intermediate of the new antidiabetic drug sitagliptine, were prepared with high enantiomeric excesses (ee≥96%) and in good yields (≥42%). The Royal Society of Chemistry 2010.

PROCESS AND INTERMEDIATES FOR THE PREPARATION OF N-ACYLATED-4-ARYL BETA-AMINO ACID DERIVATIVES

A process for producing an enantiomerically enriched, pure or enriched and essentially pure compound of Formula I [structure] wherein the R-, or S-configuration at the stereogenic center is marked with an *, which process hydrogenates an enamide compound of formula III [structure] in an organic solvent in the presence of a transition metal precursor complexed to a chiral phosphine ligand catalyst, wherein Ar is phenyl which is unsubstituted or substituted, R1 and R2 are selected from H, Cl - 8 alkyl, C5 - 12 cycloalkyl, aryl and aryl-C 1 - 2-alkyl, or R1 and R2 together with the nitrogen atom to which they are attached form a C4- r member heterocyclic πng system optionally fused with a 5- to 6- member carbocyclic or heterocyclic ring system, and the other substituents are as defined herein.