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
• Article Data: 5

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

General Description

"(R)-3-Amino-4-(2,4,5-trifluoro-phenyl)-butyric acid hydrochloride, often abbreviated as 3-ATPB, is a specific type of chemical compound. It contains elements such as carbon, hydrogen, nitrogen, fluorine, and chlorine often used in the sector of pharmaceutical chemistry. Its molecular formula is C10H11F3N1O2.ClH, and it's known for its high melting point and a molecular weight of around 290.667. This chemical compound has the unique property of being a solid under standard conditions, and it typically appears as a crystalline structure. However, it's necessary to handle it with care due to its potential hazardous effects after contact or ingestion. It's most often used in the field of medicine due to its properties and is typically synthesized rather than being naturally occurring."

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 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 1152439-73-0 2,2-dimethyl-5-[2-(2,4,5-trifluorophenyl)acetyl]-[1,3]dioxane-4,6-dione 
• 1151240-92-4 ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate 
• 1151240-88-8 3-oxo-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 
• 1151240-91-3 (3R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 1152439-74-1 (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 1374966-98-9 (S)-3-(((benzyloxy)carbonyl)amino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoicacid 

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%.

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.