1260029-44-4

Usage

Uses

Used in Organic Synthesis:
(E)-4-(2,4,5-trifluoro-phenyl)-but-2-enoic acid methyl ester is used as a reagent in organic synthesis for the creation of various drug compounds and agrochemicals. Its trifluorophenyl group enhances the biological and pharmacokinetic properties of potential drug candidates, making it a valuable building block in the development of new molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (E)-4-(2,4,5-trifluoro-phenyl)-but-2-enoic acid methyl ester serves as a key building block for the synthesis of drug compounds. Its unique structural features allow researchers to modify and optimize the properties of drug candidates, potentially leading to more effective and safer medications.
Used as a Reference Standard in Analytical Chemistry:
(E)-4-(2,4,5-trifluoro-phenyl)-but-2-enoic acid methyl ester is also utilized as a reference standard in analytical chemistry. It aids in the identification and quantification of (E)-4-(2,4,5-trifluoro-phenyl)-but-2-enoic acid and related compounds in various samples, ensuring accurate and reliable results in chemical analysis.

Upstream product

• 1260029-45-5 3-acetoxy-4-(2,4,5-trifluoro-phenyl)-butyric acid methyl ester 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 1117-71-1 methyl-4-bromo-2-butenoate 
• 1068-55-9 isopropylmagnesium chloride 
• 367-23-7 1,2,4-trifluorobenzene 
• 1117-71-1 methyl 4-bromocrotonate 
• 502462-00-2 (2,4,5-trifluorophenyl)-magnesium bromide 
• 1352613-28-5 2,4,5-trifluorobenzene magnesium chloride 

Downstream Products

• 1402569-27-0 methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(2,4,5-trifluorophenyl)-butanoate 
• 1253056-13-1 methyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate 
• 1253055-92-3 methyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate 
• 1402569-99-6 methyl 3-acetamido-4-(2,4,5-trifluorophenyl)butanoate 
• 1402569-42-9 methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(2,4,5-trifluorophenyl)-butanoate 
• 1369995-39-0 methyl 3-benzylamino-4-(2,4,5-trifluorophenyl)butanoate 
• 1414999-01-1 methyl 3-(phenoxyamino)-4-(2,4,5-trifluorophenyl)butanoate 
• 868125-58-0 methyl N-benzyloxy-4-(2,4,5-trifluorophenyl)-3(R)-aminobutanoate 
• 1402569-78-1 methyl (S)-3-(benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoate 
• 767352-29-4 (R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid 
• 1402569-24-7 methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(2,4,5-trifluorophenyl)butanoate 
• 1402569-80-5 methyl 3-(benzyloxyamino)-4-(2,4,5-trifluorophenyl) butanoate 

Relevant academic research and scientific papers

D-Glucosamine in iron-catalysed cross-coupling reactions of Grignards with allylic and vinylic bromides: Application to the synthesis of a key sitagliptin precursor

A sustainable D-glucosamine ligand is successfully introduced into iron-catalysed C-C cross-coupling reactions for the first time. The Fe(acac)2/D-glucosamine·HCl/Et3N catalytic system was effective at 5 mol% loading in coupling reactions of Grignard reagents with organic bromides. Moderate to high efficiency was achieved with preserved stereochemistry when allyl (Csp3) or alkenyl (Csp2) bromides were coupled with phenylmagnesium (Csp2) or benzylmagnesium (Csp3) bromides. The catalytic system developed was also successfully applied for the novel and economic preparation of a Michael-acceptor-like starting material used in an alternative synthesis of the drug sitagliptin, a known blockbuster for the treatment of type II diabetes mellitus.

Cobalt-Catalyzed Cross-Coupling of Grignards with Allylic and Vinylic Bromides: Use of Sarcosine as a Natural Ligand

Sarcosine was discovered to be an excellent ligand for cobalt-catalyzed carbon-carbon cross-coupling of Grignard reagents with allylic and vinylic bromides. The Co(II)/sarcosine catalytic system is shown to perform efficiently when phenyl and benzyl Grignards are coupled with alkenyl bromides. Notably, previously unachievable Co-catalyzed coupling of allylic bromides with Grignards to linearly coupled α-products was also realized with Co(II)/sarcosine catalyst. This method was used for efficient preparation of the key intermediate in an alternative synthesis of the antihyperglycemic drug sitagliptin.

PREPARATION OF SITAGLIPTIN INTERMEDIATES

The invention relates to the preparation of chiral compounds, in particular to the preparation of chiral compounds which may be used as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

Preparation of Sitagliptin Intermediates

The invention relates to the preparation of chiral compounds, in particular to the preparation of chiral compounds which may be used as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

PREPARATION OF SITAGLIPTIN INTERMEDIATES

The invention relates to the preparation of chiral compounds, in particular to the preparation of chiral compounds which may be used as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

PREPARATION OF SITAGLIPTIN INTERMEDIATES

The invention relates to the preparation of chiral compounds, in particular to the preparation of chiral compounds which may be used as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

Preparation of sitagliptin intermediates

The invention relates to the preparation of chiral compounds, in particular to the preparation of chiral compounds which may be used as intermediates for the preparation of anti-diabetic agents, preferably sitagliptin.

The asymmetric synthesis of Sitagliptin, a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

An efficient asymmetric synthesis of Sitagliptin, a new DPP-IV inhibitor for the treatment of type 2 diabetes mellitus has been developed. The beta-amino acid fragment of Sitagliptin was prepared by asymmetric Michael addition of the corresponding α, β-unsaturated ester to (R)-(α-methylbenzyl) benzylamine followed by a two-step elaboration to obtain N-boc beta-amino ester. Hydrolysis of the ester and coupling with the triazolopiperazine afforded Sitagliptin after cleavage of the N-boc group and salt formation. The overall yield was 31% over nine steps.