1151240-88-8

Basic information

• Product Name: ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate
• Synonyms: ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate;Benzenebutanoic acid, 2,4,5-trifluoro-b-oxo-, ethyl ester;WJPYOCIWVYDFDT-UHFFFAOYSA-N
• CAS NO: 1151240-88-8
• Molecular Formula: C₁₂H₁₁F₃O₃
• Molecular Weight: 260.2091496
• EINECS: -0
• Mol File: 1151240-88-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 290.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.291±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 9.97±0.46(Predicted)
• CAS DataBase Reference: ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate(1151240-88-8)
• EPA Substance Registry System: ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate(1151240-88-8)

Safety Data

• Hazardous Substances Data: 1151240-88-8(Hazardous Substances Data)

Usage

Description

Ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate is an organic compound that serves as an intermediate in the synthesis of various chemical products. It is characterized by its unique molecular structure, which features a 3-oxo (keto) group and a 2,4,5-trifluorophenyl group attached to a butanoate backbone. ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate is known for its potential applications in the pharmaceutical and chemical industries due to its versatile chemical properties.

Uses

Used in Pharmaceutical Industry:
Ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate is used as a key intermediate in the synthesis of racemic beta-amino esters. These beta-amino esters are crucial for the preparation of enantiomeric beta-amino acids, which are essential building blocks in the development of various pharmaceutical compounds. The application of this compound in the pharmaceutical industry is significant, as it contributes to the creation of new drugs with potential therapeutic benefits.
Used in Chemical Industry:
In the chemical industry, ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate is utilized as a starting material for the synthesis of various specialty chemicals. Its unique structure allows for further functionalization and modification, making it a valuable component in the development of new chemical products with specific applications in areas such as materials science, agrochemicals, and coatings.

Upstream product

• 64-17-5 ethanol 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 105-53-3 diethyl malonate 
• 220141-74-2 2-(2,4,5-trifluorophenyl)acetonitrile 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 105-36-2 ethyl bromoacetate 
• 1176895-65-0 2-(2,4,5-trifluorophenyl)acetyl chloride 
• 6148-64-7 ethyl potassium malonate 
• 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 

Downstream Products

• 1151240-89-9 3-amino-4-(2,4,5-trifluorophenyl)-but-2-enoic acid ethyl ester 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 1151240-91-3 (3R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 1151240-92-4 ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate 
• 1204818-19-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride 
• 1204818-18-7 (S)-β-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester di-p-toluoyl-L-tartaric acid salt 
• 1152439-74-1 (R)-3-tertbutoxycarbonylamino-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 
• 764667-65-4 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione 
• 486460-32-6 sitagliptin 
• 1349649-83-7 (R)-2-methyl-N-((R)-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4] triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)propane-2-sulfinamide 
• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 1242332-75-7 (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid choline salt 
• 1242332-69-9 (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo [1,5-a]pyrazine-1-carboxylic acid triethyl amine salt 

Relevant articles and documents

Substrate screening of amino transaminase for the synthesis of a sitagliptin intermediate

We reported herein a new enzymatic route to synthesize a sitagliptin intermediate using an aminotransferase. Substrate profile indicated that hydroxyethyl-3-oxo-4-(2,4,5-trifluorophenyl)butanoate, among 11 analogs, showed the best biocatalytic performance, partially due to its best solubility in the enzymatic system. The corresponding amino esters showing strong product inhibition on the reaction, were inclined to autohydrolyze, thus driving the reaction forward, which indicated the contribution of the rapid hydrolysis of hydroxyethyl ester to the biocatalytic performance. The reaction was performed at 100?mM with 82% conversion in 24?h. The amino ester product was further transformed to Boc-(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid, the key intermediate of sitagliptin.

Sitagliptin synthesis method

The invention discloses a sitagliptin synthesis method, which comprises: carrying out a reaction on a compound represented by a formula IV, (R)-(+)-tert-butyl sulfinamide and hydrogen under the catalysis of a catalyst to obtain a compound represented by a formula V; and carrying out a hydrolysis reaction on the compound represented by the formula V to obtain a compound represented by a formula VI,ie., sitagliptin. According to the present invention, the method has advantages of easily available raw materials, simple steps, high yield and mild reaction conditions, and is suitable for industrial production. The formulas IV, V and VI are defined in the specification.

Preparation method of sitagliptin intermediate

The invention belongs to the field of pharmaceutical synthesis, and particularly relates to a preparation method of a sitagliptin intermediate. The preparation method includes the steps of 1) acylating chlorination reaction: enabling 2,4,5-trifluorophenylacetic acid to directly react with sulfoxide chloride to generate a compound II; 2) Grignard reagent preparation: adding a compound III and magnesium chips, and triggering with iodine to obtain a Grignard reagent compound IV; 3) Grignard reaction: taking cuprous iodide as a catalyst, subjecting the compound II and the Grignard reagent compound IV to Grignard reaction to generate the sitagliptin intermediate-a compound V. The preparation method of the sitagliptin intermediate is simple in synthetic route, capable of producing highly-pure product, high in yield, low in cost, mild in reaction conditions, and applicable to industrialized production.