486460-23-5

Basic information

• Product Name: Sitagliptin N-Boc IMpurity
• Synonyms: Sitagliptin N-Boc IMpurity;Boc-Sitagliptin;N-Boc-Sitagliptin;(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-yl)carbamate;Sitagliptin Impurity 22;tert-Butyl N-[(2R)-4-oxo-4-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-1-(2,4,5-trifluorophenyl)butan-2-yl]carbamate;Sitagliptin N-Boc;tert-butyl (R)-(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-yl)carbamate
• CAS NO: 486460-23-5
• Molecular Formula: C₂₁H₂₃F₆N₅O₃
• Molecular Weight: 507.4294392
• EINECS: 1312995-182-4
• Mol File: 486460-23-5.mol
• Article Data: 49

Chemical Properties

• Melting Point: 188-191 °C(Solv: toluene (108-88-3))
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 11.60±0.46(Predicted)
• CAS DataBase Reference: Sitagliptin N-Boc IMpurity(CAS DataBase Reference)
• NIST Chemistry Reference: Sitagliptin N-Boc IMpurity(486460-23-5)
• EPA Substance Registry System: Sitagliptin N-Boc IMpurity(486460-23-5)

Safety Data

• Hazardous Substances Data: 486460-23-5(Hazardous Substances Data)

Usage

Description

Sitagliptin N-Boc IMpurity, also known as N-Boc-Sitagliptin, is the N-Boc protected derivative of Sitagliptin (S490990), a dipeptidyl peptidase-4 (DPP-4) inhibitor. It plays a crucial role in the development and synthesis of Sitagliptin, which is a medication used for glycemic control in patients with type 2 diabetes.

Uses

Used in Pharmaceutical Industry:
Sitagliptin N-Boc IMpurity is used as an intermediate compound for the synthesis of Sitagliptin, a DPP-4 inhibitor, which is essential for glycemic control in patients with type 2 diabetes. Sitagliptin N-Boc IMpurity helps in the development of Sitagliptin by providing a protective N-Boc group that prevents unwanted side reactions during the synthesis process.
Used in Research and Development:
Sitagliptin N-Boc IMpurity is also used in research and development for the study of DPP-4 inhibitors and their potential applications in the treatment of type 2 diabetes. Researchers can use this compound to investigate the structure-activity relationship of Sitagliptin and other related compounds, leading to the discovery of more effective and safer treatments for diabetes.
Used in Quality Control:
In the pharmaceutical manufacturing process, Sitagliptin N-Boc IMpurity is used for quality control purposes. It helps ensure that the final product, Sitagliptin, meets the required purity and potency standards. By monitoring the presence and concentration of this impurity, manufacturers can maintain the quality and consistency of Sitagliptin in the final drug product.

Upstream product

• 486460-21-3 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 157911-56-3 2,4,5-trifluorobenzyl bromide 
• 486460-20-2 3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine 
• 486460-08-6 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate 
• 486460-07-5 (2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine 
• 486460-25-7 [3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester 
• 486460-09-7 (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid 
• 762240-92-6 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride 
• 1234321-84-6 (Z)-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)-but-2-en-2-ylcarbamate 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 1242242-72-3 (S)-tert-butyl 1-iodo-4-oxo-4-(3-(tnfluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazin-7-yl)butan-2-ylcarbamate 
• 881995-73-9 3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 

Downstream Products

• 486460-32-6 sitagliptin 
• 486459-71-6 Sitagliptin hydrochloride 
• 486459-71-6 (2R)-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-amine hydrochloride 
• 654671-78-0 sitagliptin phosphate 
• 654671-78-0 (2R)-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-amine phosphate 
• 881995-69-3 (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 

Relevant articles and documents

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 method of sitagliptin free alkali

The invention belongs to the field of organic chemistry, and particularly discloses a synthesis method of sitagliptin free alkali. The synthesis method comprises the following specific steps: (1) dissolving (3R)-N-tert-butyloxycarbonyl-3-amino-4-(2,4,5-trifluorophenyl) butyric acid and organic alkali in an organic solvent, adding a phosphorus-containing condensing agent, then adding 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazol[4,3-alpha]pyrazine hydrochloride to prepare a compound represented by a formula (II); and (2) removing t-butyloxycarboryl from the compound shown in the formula II under the action of acid to obtain a compound I namely sitagliptin free alkali. The method is mild in process reaction condition, easy to control, short in reaction time, free of extraction, simple to operate and beneficial to industrial production, and the process cost is reduced; and the prepared compound shown in the formula I is high in yield, high in purity and free of heavy metal residues.

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.