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

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

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 
• 220141-74-2 2-(2,4,5-trifluorophenyl)acetonitrile 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 105-36-2 ethyl bromoacetate 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 105-53-3 diethyl malonate 
• 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

• 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 
• 1242332-84-8 (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-(2S)-2-amino-5-carbamimidamidopentanoic acid 

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.

Method for preparing Sitagliptin intermediate

The invention belongs to the field of organic synthesis and particularly relates to a method for preparing a Sitagliptin intermediate. The intermediate has a structure represented by a formula A shownin the description, wherein R1 and R2 are the same, or are differently hydrogen or C1-C5 alkyl, more preferably, R1 is tert-butyl, and R2 is hydrogen.

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.

West geleg sandbank intermediate preparation method

The invention relates to a preparation method of a sitagliptin intermediate. The method utilizes a low-toxicity organic solvent as a reaction solvent, realizes high-yield preparation of a high-purity desired product, is conducive to safe production and is suitable for industrial production.

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.

TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE DERIVATIVES SALTS, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

The present invention relates to (R)-7-[3-Amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid pharmaceutical salts, methods for their preparation, pharmaceutical compositions containing the same and their use as a therapeutic agent, especially as a dipeptidyl peptidase IV inhibitor.

Preparation method of optically pure 3-hydroxyl-4-(2,4,5-trifluorophenyl)ethyl butyrate

Provided is a preparation method of optically pure 3-hydroxyl-4-(2,4,5-trifluorophenyl)ethyl butyrate. The method comprises the steps that a conversion reaction is conducted on 2,4,5-trifluoro phenyl acetic acid to prepare 3-oxo-4-(2,4,5-trifluorophenyl)e

TETRAHYDRO-IMIDAZO[1,5-a]PYRAZINE DERIVATIVES SALTS, PREPARATION METHODS AND MEDICINAL USE THEREOF

Pharmaceutically acceptable salts of (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-formic acid, their preparation methods, compositions containing the said pharmaceutical salts and their use as medicaments, especially as dipeptidyl peptidase IV (DPP-IV) inhibitors are disclosed.

SALTS OF TETRAHYDROIMIDAZO Y1,5-A¨PYRAZINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL USE THEREOF

Pharmaceutical salts of (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-formic acid, their preparation methods, compositions containing the said pharmaceutical salts and their use as medicaments, especially as dipeptidyl peptidase IV (DPP-IV) inhibitors are disclosed.

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%.