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

• 209995-38-0 (2,4,5-trifluorophenyl)acetic acid 
• 764667-64-3 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1151240-91-3 (3R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester 
• 1276113-61-1 (R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate 
• 1380243-15-1 C₁₁H₂₃NO₅ 
• 915715-25-2 (S)-(3-benzyloxy-1-hydroxymethyl-propyl)-carbamic acid tert-butyl ester 

Downstream Products

• 1321614-27-0 tert-butyl (4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-47-4 tert-butyl N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-(4S)-4-{[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-prolinate 
• 1321614-52-1 (4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}butanoyl]-L-proline 
• 1321614-50-9 N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-norvalyl-(4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-proline 
• 1321614-53-2 N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-norleucyl-(4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-proline 
• 1321614-40-7 N-[(1S)-1-carboxy-3-phenylpropyl]-L-alanyl-(4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-proline 
• 1321614-54-3 (4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}butanoyl]-L-proline 
• 1321614-51-0 N-[(1S)-1-carboxy-3-phenylpropyl]-L-norvalyl-(4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-proline 
• 1321614-55-4 N-[(1S)-1-carboxy-3-phenylpropyl]-L-norleucyl-(4S)-4-{[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]amino}-L-proline 
• 1395398-12-5 C₂₅H₂₈ClF₃N₄O₄ 
• 1395398-09-0 C₂₈H₃₀F₃N₅O₄ 
• 1395398-03-4 C₂₉H₃₃F₃N₄O₄ 
• 1395397-97-3 C₂₉H₃₁F₃N₄O₆ 
• 1395397-91-7 C₂₅H₂₉F₃N₄O₅ 

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.

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.

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.

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.

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.

Preparation method of sitagliptin intermediate

The invention discloses a preparation method of a sitagliptin intermediate and belongs to the field of medicine synthesis. The invention provides a preparation method of a compound 2; the compound 2 is prepared without the need of a catalyst and a resolving agent which have a high price and harsh low-temperature conditions, so that the cost is reduced to the great extent; the preparation method has the advantages of simple technology, high purity and high yield and is suitable for mass production.

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.