881995-73-9

Usage

Uses

Used in Pharmaceutical Industry:
Benzenebutanoic acid, b-[[(1,1-dimethylethoxy)carbonyl]amino]-2,4,5-trifluoro-, methyl ester, (bR)is used as a pharmaceutical intermediate for the synthesis of various drug candidates. The presence of the trifluoromethyl group can enhance the lipophilicity, metabolic stability, and bioavailability of the resulting drug molecules, making it a valuable building block in the development of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, Benzenebutanoic acid, b-[[(1,1-dimethylethoxy)carbonyl]amino]-2,4,5-trifluoro-, methyl ester, (bR)is used as a precursor for the synthesis of agrochemicals, such as herbicides, insecticides, and fungicides. The trifluoromethyl group can improve the compound's volatility, solubility, and target specificity, leading to more effective and environmentally friendly agrochemical products.
Used in Materials Science:
Benzenebutanoic acid, b-[[(1,1-dimethylethoxy)carbonyl]amino]-2,4,5-trifluoro-, methyl ester, (bR)is used as a key component in the development of advanced materials, such as polymers, coatings, and adhesives. The trifluoromethyl group can impart unique properties to these materials, such as increased thermal stability, chemical resistance, and adhesion, making them suitable for various high-performance applications.

Upstream product

• 881995-69-3 (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1151240-93-5 3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)but-2-enoic acid methyl ester 
• 1234321-77-7 (Z)-3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)-2-butenoic acid methyl ester 
• 1253055-94-5 (R)-(-)-mandelic acid salt of (R)-methyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate 
• 1284306-20-2 (S)-methyl 3-(Boc-amino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoate 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 1276113-56-4 methyl (3 S)-3-(tert-butoxycarbonylamino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate 
• 909295-29-0 methyl (S)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoate 
• 1276113-66-6 (R)-methyl 3-(tert-butoxycarbonylamino)-4-(trifluoromethanesulfonyloxy)-4-(2,4,5-trifluorophenyl)butyrate 
• 1361050-70-5 (R)-4-methoxy-4-oxo-2-(2,4,5-trifluorobenzyl)butanoic acid 
• 75-65-0 tert-butyl alcohol 
• 1276113-62-2 (S)-methyl 3-(tert-butoxycarbonylamino)-4-(trifluoromethanesulfonate)-4-(2,4,5-trifluorophenyl)-n-butyrate 
• 1361050-65-8 (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate 

Downstream Products

• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 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 
• 1048703-14-5 (R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate 
• 1500076-58-3 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)benzamide hydrochloride 
• 1500076-59-4 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-2,3-difluorobenzamide hydrochloride 
• 1500076-60-7 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-methoxybenzamide hydrochloride 
• 1500076-61-8 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-(methylsulfonyl)-benzamide hydrochloride 
• 1500076-62-9 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-sulfamoylbenzamide hydrochloride 
• 1500076-63-0 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-(trifluoromethyl)benzamide hydrochloride 
• 1500076-64-1 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-4-(1H-1,2,4-triazol-1-yl)benzamidehydrochloride 
• 1500076-65-2 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-1H-benzo[d]imidazole-6-carboxamide hydrochloride 
• 1500076-66-3 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)-1H-benzo[d]-[1,2,3]triazole-6-carboxamide hydrochloride 
• 1500076-67-4 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)nicotinamide hydrochloride 
• 1500076-68-5 (R)-N-(3-amino-4-(2,4,5-trifluorophenyl)butyl)thiophene-3-carboxamide hydrochloride 

Relevant academic research and scientific papers

Nickel-Catalyzed Asymmetric Hydrogenation for the Synthesis of a Key Intermediate of Sitagliptin

Nickel-catalyzed enantioselective hydrogenation of enamines leading to the efficient synthesis of 3-R-Boc-amino-4-(2,4,5-trifluorophenyl)butyric esters, the key intermediate of the blockbuster antidiabetic drug (R)-SITAGLIPTIN, is described. The sitagliptin motifs were isolated in more than 99% yield and with 75–92% ee using the earth-abundant nickel catalyst. Upon chiral resolution with (R)- and (S)-1-phenylethylamines, the partially enantioenriched (R)- and (S)-Boc-3-amino-4-(2,4,5-trifluorophenyl)butanoic acids provided >99.5% ee of the crucial sitagliptin intermediate. The asymmetric hydrogenation protocol was scaled up to 10 g with consistency in yield and ee, and has been reproduced in multiple batches.

Preparation method of chiral 4 - aryl - β β-amino acid derivative

Provided is a method for preparing a chiral 4-aryl-β-amino acid derivative. The preparation method comprises hydrogenating an enamine compound having a structure as shown in Formula III in an organic solvent in the presence of a catalyst containing a transition metal and BIBOPs. The preparation method of the present invention uses a small amount of a selected asymmetric catalyst, and has a simple operation, mild reaction conditions, a high yield, a high stereoselectivity, and better industrial application and economic values.

A west he row sandbank chiral intermediate and asymmetric synthesis method

The invention relates to a sitagliptin chiral intermediate and an asymmetric synthesis method thereof. The asymmetric synthesis method comprises the steps: with 2,4,5-trifluorophenyl acetic acid as a starting material, carrying out a reduction reaction to obtain 2-(2,4,5-trifluorophenyl)ethanol, then carrying out a reaction with an oxidant, carrying out condensation of the product without separation and (R)-(+)-tert-butyl sulfinamide to obtain corresponding acetal, carrying out a reaction of the obtained product with dialkyl malonate to obtain a key chiral intermediate, hydrolyzing to obtain a corresponding organic amine, carrying out a reaction of the amine with caustic alkali and then acidifying to obtain a corresponding carboxylic acid, then carrying out condensation with 3-(trifluoromethyl)-5,6,7,8- tetrahydro-[1,2,4] triazolo[4,3-a]pyrazine hydrochloride to obtain sitagliptin tert-butyl oxanamide, and finally deprotecting with hydrochloric acid to obtain sitagliptin. The yields of all the steps are all higher, the used reagents are all conventional cheap reagents, no expensive chiral catalysts are used, the reaction conditions are quite mild, and the asymmetric synthesis method is suitable for industrialization.

Glucovance west Geleg sandbank intermediate process for the preparation of amino acid derivatives

The invention discloses a preparation method of a new diabetes drug sitagliptin intermediate aminobenzene butyric acid derivative. The preparation method comprises the following steps of: (1) mixing a compound shown in a formula I with R(+)-alpha-phenethyl and acetic acid to obtain a compound shown in a formula II; (2) mixing the compound shown in the formula II with sodium borohydride and protonic acid or lewis acid to obtain a compound shown in a formula III; (3) mixing the compound shown in the formula III with X to obtain a compound shown in a formula IV; (4) mixing the compound as shown in the formula IV with an inorganic base 1 to obtain a compound shown in a formula V; (5) obtaining a compound shown in a formula VI by the compound shown in the formula V; and (6) mixing the compound shown in the formula VI with an inorganic base 2 to obtain a compound shown in a formula VII.

Sitagliptin intermediate preparation method

The invention relates to the technical field of organic chemistry and especially relates to a sitagliptin intermediate preparation method. The invention provides a compound with a structure shown in the formula 6. The sitagliptin intermediate shown in the formula 8 and prepared from the compound with a structure shown in the formula 6 has high HPLC purity and an ee value of 99% or more.

SITAGLIPTIN INTERMEDIATES, PREPARATION METHODS AND USES THEREOF

The present invention relates to Sitagliptin intermediate and preparation method and use thereof. The method comprises reacting compound of formula (II) and trifluorobromobenzene with a Grignard reagent by a Grignard reaction to obtain a compound of formula (I). Compound of formula (I) is a new intermediate compound for the synthesis of Sitagliptin. Compound of formula (I) can be easily used for preparing another important intermediate compound of formula (V) for the synthesis of Sitagliptin. The structures of the compounds mentioned above are as the following:

SITAGLIPTIN INTERMEDIATES, PREPARATION METHODS AND USES THEREOF

The present invention relates to Sitagliptin intermediate and preparation method and use thereof. The method comprises reacting compound of formula (II) and trifluorobromobenzene with a Grignard reagent by a Grignard reaction to obtain a compound of formula (I). Compound of formula (I) is a new intermediate compound for the synthesis of Sitagliptin. Compound of formula (I) can be easily used for preparing another important intermediate compound of formula (V) for the synthesis of Sitagliptin. The structures of the compounds mentioned above are as the following:

Process for the production of sitagliptin

The present invention is directed to a process for the preparation of Sitagliptin, having formula (I)

Synthesis of a chiral β-amino acid derivative by a cobalt-catalysed coupling reaction

A chiral β-amino acid derivative was synthesised by a cobalt-catalysed alkylation of 2,4,5-trifluorophenyl magnesium bromide with the alkyl halide derivative of L-aspartic acid, using an efficient catalytic reagent: CoCl 2/TMEDA. The halide der

The synthesis of a chiral β-amino acid derivative by the Grignard reaction of an aspartic acid equivalent

A novel synthetic route to chiral β-amino acid derivative has been developed by a Grignard reaction of 2,4,5-trifluo- rophenyl magnesium bromide with the Weinreb amide derivative of L-aspartic acid. The aspartic equivalent was synthesised from L-aspartic