1151240-91-3

Basic information

• Product Name: (R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl
• Synonyms: (R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl
• CAS NO: 1151240-91-3
• Molecular Weight: 261.244
• Mol File: 1151240-91-3.mol

Chemical Properties

• CAS DataBase Reference: (R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl(1151240-91-3)
• EPA Substance Registry System: (R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl(1151240-91-3)

Safety Data

• Hazardous Substances Data: 1151240-91-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biotechnology Research and Development:
(R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl is used as a key intermediate in the synthesis and study of peptides and proteins. Its unique trifluoromethyl group allows for the exploration of novel bioactive compounds with potential therapeutic applications.
Used in Medicinal Chemistry Applications:
In the field of medicinal chemistry, (R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl is utilized as a building block for the development of new pharmaceuticals. The trifluoromethyl group in its structure can influence the pharmacokinetic and pharmacodynamic properties of the resulting compounds, potentially leading to improved drug candidates.
Used in Chemical Synthesis:
(R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl serves as a versatile reagent in organic synthesis, enabling the preparation of a variety of fluorinated compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Peptide Synthesis:
As an analog of phenylalanine, (R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl is used in the synthesis of modified peptides with altered biological activities. These modified peptides can be employed in research to study the structure-function relationships of peptides and proteins, as well as in the development of peptide-based drugs with improved properties.

Upstream product

• 1151240-88-8 3-oxo-4-(2,4,5-trifluorophenyl)-butyric acid ethyl ester 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 913623-45-7 1,2,4-trifluoro-5-(2-nitrovinyl)-benzene 
• 1204818-17-6 (R)-β-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester di-p-toluoyl-D-tartaric acid salt 
• 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 
• 1151240-89-9 3-amino-4-(2,4,5-trifluorophenyl)-but-2-enoic acid ethyl ester 

Downstream Products

• 1152439-74-1 (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 1204818-19-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride 
• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 654671-78-0 sitagliptin phosphate 
• 486460-32-6 sitagliptin 
• 486460-23-5 (R)-tert-butyl 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-ylcarbamate 

Relevant articles and documents

Purpose of compound for preparing Sitagliptin and Sitagliptin preparation method

The invention provides a compound shown by a formula I, a purpose of a stereoisomer, a geometrical isomer, a tautomer, an oxynitride, a hydrate, a solvate, a metabolite, a pharmacologically acceptable salt or prodrug of the compound in Sitagliptin preparation, and a Sitagliptin preparation method. The formula I is shown in the description, wherein R1 is a substitutional group containing the hydroxyl group. The compound shown by the formula I or the stereoisomer, the geometrical isomer, the tautomer, the oxynitride, the hydrate, the solvate, the metabolite, the pharmacologically acceptable salt or the prodrug of the compound shown by the formula I has high water solubility, and is used for obtaining a chiral amino intermediate to further obtain the Sitagliptin. Compared with the prior art, the compound has the advantages that the amino group conversion rate is greatly improved; the yield of the Sitagliptin is also greatly improved.

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.

CHIRAL AMINES, A PROCESS FOR PREPARATION AND USE THEREOF

Described herein is the general synthesis of chiral amine from vinyl nitro compounds using Josiphos catalyst. The process is applied to develop a novel route to Sitagliptin (a DPP-IV inhibitor).

A NOVEL PROCESS FOR THE PREPARATION OF SITAGLIPTIN

The present invention is directed to a process for the preparation of enantiomerically enriched β-amino acid derivatives which are important chiral building blocks and intermediates in pharmaceuticals. More specifically, the invention pertains to a novel process for practically convenient and economically producing enantiomerically enriched β-amino acid derivatives which are useful for the synthesis of amide inhibitors of dipeptidyl peptidase IV like Sitagliptin, which have been used to treat type 2 diabetes.

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.

PREPARATION OF SITAGLIPTIN INTERMEDIATE

Intermediate compounds in the synthesis of Sitagliptin, 3-amino-4-(2,4,5- trifluorophenyl)but-2-enoic acid alkyl ester, and amino protected-3-amino-4-(2,4,5- trifluorophenyl)but-2-enoic acid alkyl ester, and the stereoselective reduction of these compound to give Synthon I, or the amino-protected Synthon I, are provided.