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

• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 762240-92-6 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride 
• 936630-57-8 (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 75-65-0 tert-butyl alcohol 
• 486460-21-3 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine 
• 1259320-64-3 2-(R)-4-oxo-2-(2,4,5-trifluorobenzyl)-4-(3-trifluoromethyl-5,6-dihydro[1,2,4]triazolo[4,3-a]-7(8H)-pyrazinyl)butyric acid 
• 881995-73-9 3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 
• 883267-70-7 2-(2,4,5-trifluorophenyl)ethanol 
• 767352-29-4 (R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid 
• 1380521-84-5 tert-butyl (E)-4-(2',4',5'-trifluorophenyl)but-2-enoate 
• 1361389-75-4 3(R)-3-[(benzyloxy)amino]-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 486460-32-6 sitagliptin 
• 111991-20-9 2-(2,4,5-trifluorophenyl)acetaldehyde 

Downstream Products

• 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 
• 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 
• 486459-71-6 Sitagliptin hydrochloride 
• 486460-32-6 sitagliptin 

Relevant articles and documents

Process for preparing sitagliptin

The present technology relates to a method for manufacturing sitagliptin, which is a representative drug among DPP-4 inhibitors which are drugs used for the treatment of diabetes. The method of the present invention uses CDI for the condensation reaction of specific compounds, and through a specific subsequent process, high-purity sitagliptin phosphate monohydrate can be manufactured in a high yield. In particular, the manufacturing method of the present invention is suitable for mass production.

Synthesis method of sitagliptin free alkali and sitagliptin phosphate monohydrate

The invention relates to a synthesis method of sitagliptin free alkali and sitagliptin phosphate monohydrate. According to the method, dry HOBt is removed or changed into HOBt hydrate, a solvent DMF is removed in the process, and a simple solvent easy to recover is used in the production process, so that the production cost is reduced, and the reaction safety is improved. According to the invention, with the in-situ process from a compound represented by a formula 2 to a compound represented by a formula 6, the yield can be improved, the operation steps can be reduced, and the methanol or isopropanol IPA is replaced with other solvents so as to avoid the generation of impurities represented by a formula 7, a formula 8 and a formula 9, such that the product purity and the yield can be substantially improved, and the HPLC purity of the sitagliptin free alkali is more than 99%.

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.