1151240-92-4

Basic information

• Product Name: ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate
• Synonyms: ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate
• CAS NO: 1151240-92-4
• Molecular Weight: 261.244
• Mol File: 1151240-92-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate(1151240-92-4)
• EPA Substance Registry System: ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate(1151240-92-4)

Safety Data

• Hazardous Substances Data: 1151240-92-4(Hazardous Substances Data)

Upstream product

• 1151240-88-8 3-oxo-4-(2,4,5-trifluorophenyl)-butyric acid ethyl ester 
• 1152439-73-0 2,2-dimethyl-5-[2-(2,4,5-trifluorophenyl)acetyl]-[1,3]dioxane-4,6-dione 
• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 1151240-89-9 3-amino-4-(2,4,5-trifluorophenyl)-but-2-enoic acid ethyl ester 

Downstream Products

• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 1151240-90-2 (S)-ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate 
• 1204818-17-6 (R)-β-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester di-p-toluoyl-D-tartaric acid salt 
• 1204818-18-7 (S)-β-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester di-p-toluoyl-L-tartaric acid salt 
• 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 
• 1204818-19-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride 
• 1152439-74-1 (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 1449289-61-5 C₁₂H₁₄F₃NO₂*C₁₁H₁₃NO₃ 
• 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

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.

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.