922178-94-7

Usage

Uses

Used in Pharmaceutical Industry:
BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID is used as a key reactant for the preparation of peptidase IV inhibitors, which are important in the development of medications for the treatment of type 2 diabetes and other metabolic disorders. Peptidase IV inhibitors help regulate the digestion and absorption of carbohydrates, thereby managing blood sugar levels effectively.
As a chemical intermediate, BOC-(S)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID plays a significant role in the synthesis of bioactive molecules, contributing to advancements in medicinal chemistry and drug discovery. Its specific properties allow for targeted modifications and enhancements of peptidase IV inhibitors, potentially leading to more effective treatments and improved patient outcomes.

Upstream product

• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1204818-19-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride 
• 881995-69-3 (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 
• 1361050-65-8 (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate 
• 1361050-69-2 4-methoxy-4-oxo-2-(2,4,5-trifluorobenzyl)butanoic acid 
• 1361050-70-5 (R)-4-methoxy-4-oxo-2-(2,4,5-trifluorobenzyl)butanoic acid 
• 501-52-0 3-Phenylpropionic acid 
• 1246220-99-4 (R)-tert-butyl (1-hydroxy-3-(2,4,5-trifluorophenyl)propan-2-yl)carbamate 
• 130622-08-1 (2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester 
• 397246-14-9 (1-(hydroxymethyl)-3-hydroxypropyl)carbamic acid tert-butyl ester 
• 322691-00-9 2-(tert-butoxycarbonylamino)-butane-1,4-diyl dimethanesulfonate 

Downstream Products

• 1395397-56-4 C₂₇H₂₉F₆N₃O₄ 
• 1395398-00-1 C₂₈H₃₀F₃N₃O₄S 
• 1395398-15-8 C₃₁H₃₂F₄N₄O₄ 
• 1395398-21-6 C₂₅H₂₇F₅N₄O₄ 
• 1395398-18-1 C₂₅H₂₈F₄N₄O₄ 
• 1395397-13-3 C₂₇H₃₄F₃N₃O₄ 
• 1395395-57-9 C₂₂H₂₆F₃N₃O₂ 
• 1395397-52-0 C₂₇H₂₉F₆N₃O₅ 
• 910551-58-5 C₂₆H₃₁F₃N₄O₆S 
• 910550-48-0 t-butyl [(2R)-4-[4-(4-carboxybenzoyl)-1-piperazinyl]-1-(2,4,5-trifluorophenyl)-4-oxobutyl]carbamate 
• 910550-98-0 C₂₇H₃₀F₃N₃O₆ 
• 1395397-68-8 C₃₁H₄₀F₃N₅O₄ 
• 1395397-75-7 C₂₉H₃₁F₃N₄O₄ 
• 1395397-79-1 C₂₉H₃₂F₃N₃O₆ 

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.

Synthesis of (?)-(R)-Sitagliptin by RhI-Catalyzed Asymmetric Hydroamination

We report of a concise synthesis of (R)-sitagliptin monophosphate – a drug predominantly applied in the treatment of type 2 diabetes. Utilizing our recently developed RhI-catalyzed hydroamination of allenes for the stereoselective construction of the inherent chiral amino function, a new approach to (R)-sitagliptin monophosphate on a 3.5 mmol scale was established.

Synthesis of (R)-3-(tert-Butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic Acid, a Key Intermediate, and the Formal Synthesis of Sitagliptin Phosphate

An alternate formal synthesis of Sitagliptin phosphate is disclosed from 2,4,5-trifluorobenzadehyde in 8 linear steps with an overall yield of 31%. The chiral β-amino acid moiety present in sitaglitpin is installed via an asymmetric hydrogenation followed by a stereoselective Hofmann rearrangement as the key steps. The key chiral intermediate Boc-amino acid 1 prepared by this novel route was further converted to Sitagliptin phosphate following the known literature protocol.

Preparation method of 1-morpholinyl-4-(2,4,5-trifluorophenyl)butane-1,3-dione

The invention discloses a preparation method of 1-morpholinyl-4-(2,4,5-trifluorophenyl)butane-1,3-dione, and belongs to the technical field of organic synthesis. The preparation method comprises the following step: under the action of a metal chelating agent and an alkali, carrying out a reaction of the following formula on a compound 2 and a compound 3 in an organic solvent to obtain a compound 1. The preparation method disclosed by the invention is high in yield, simple in post-treatment, simple, feasible, mild in reaction condition and suitable for industrial production.

Preparation method of 1,3-dicarbonyl compound and intermediate of the 1,3-dicarbonyl compound

The invention discloses a preparation method of a 1,3-dicarbonyl compound and an intermediate of the 1,3-dicarbonyl compound, and particularly discloses a preparation method of a compound as shown ina formula I. The preparation method comprises the following step: in a solvent, performing an elimination reaction as shown in the specification on a compound as shown in a formula II to obtain the compound as shown in the formula I, wherein R is a tert-butoxy group, a methoxy group, an ethoxy group or a methyl group. The preparation method disclosed by the invention is relatively low in cost andbeneficial to industrial production.

AN IMPROVED PROCESS FOR THE PREPARATION OF SITAGLIPTIN AND ITS INTERMEDIATES

The present invention relates to a process for the preparation of novel intermediates useful for the preparation of Sitagliptin or its pharmaceutically acceptable salts. The present invention relates to an efficient process for the preparation of Sitagliptin intermediates. The present invention relates to an improved process for the preparation of Sitagliptin or its pharmaceutically acceptable salts.

BOC-(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid condensation impurity and preparation method thereof

The invention provides a sitagliptin phosphate important intermediate BOC-(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid condensation impurity and a preparation method and preparation thereof. TheBOC-(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid condensation impurity and the preparation method thereof have important significance for the following industrial production of bulk drugs.

Method for synthesizing sitagliptin and intermediate thereof through biological catalysis

The invention provides a method for synthesizing sitagliptin and an intermediate thereof through biological catalysis, and particularly provides compounds as shown in formula I and a formula II, or pharmaceutically acceptable salt thereof, polypeptide capable of synthesizing a compound as shown in the formula I to produce a compound as shown in the formula II, nucleic acid coding the polypeptide,and a vector and a cell containing the nucleic acid. In addition, the invention further provides a method for producing the compound as shown in the formula II and sitagliptin through the polypeptideand the compound as shown in the formula I, and a preparation method for preparing the polypeptide.

(S)-2-amino-3-(2,4,5-trifluorophenyl)propionic acid menthyl ester hydrochloride and preparation method and application thereof

The invention provides (S)-2-amino-3-(2,4,5-trifluorophenyl)propionic acid menthyl ester hydrochloride and a preparation method and application thereof and belongs to the technical field of medicinalchemistry. According to the technical problem of low synthesis efficiency of sitagliptin is solved. The technical scheme is that the structural formula of the (S)-2-amino-3-(2,4,5-trifluorophenyl)propionic acid menthyl ester hydrochloride is in the description below. The (S)-2-amino-3-(2,4,5-trifluorophenyl)propionic acid menthyl ester hydrochloride has the advantages that the (S)-2-amino-3-(2,4,5-trifluorophenyl)propionic acid menthyl ester hydrochloride is a novel compound, raw materials used for preparation are cheap and easy to obtain, the process is simple, and the yield is as high as 83.3%.