1352613-30-9

Basic information

• Product Name: (S)-3-hydroxy-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
• Synonyms: (S)-3-hydroxy-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
• CAS NO: 1352613-30-9
• Molecular Weight: 408.303
• Mol File: 1352613-30-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-3-hydroxy-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-hydroxy-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one(1352613-30-9)
• EPA Substance Registry System: (S)-3-hydroxy-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one(1352613-30-9)

Safety Data

• Hazardous Substances Data: 1352613-30-9(Hazardous Substances Data)

Upstream product

• 327-52-6 1-bromo-2,4,5-trifluorobenzene 
• 868071-17-4 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid 
• 486460-21-3 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine 
• 1283096-74-1 (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile 
• 1246960-15-5 (S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol 
• 1352613-29-6 (S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate 
• 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 
• 764667-65-4 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione 

Downstream Products

• 1352613-31-0 (S)-3-(methanesulfonyloxy)-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one 
• 1253055-98-9 (R)-3-azido-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 
• 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 
• 486460-32-6 sitagliptin 
• 1433545-29-9 (R)-N-(4-methylphenylsulfonyl)-N-(t-butoxycarbonyl)-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 
• 1433545-80-2 (S)-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 p-toluenesulfonate 
• 823817-55-6 (S)-Sitagliptin 
• 654671-78-0 sitagliptin phosphate 
• 823817-56-7 (R/S)-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 
• 1433546-25-8 (S)-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 acetate 
• 1433546-13-4 (S)-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 p-nitrobenzenesulfonate 
• 1433545-91-5 (S)-diethyl (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)phosphate 

Relevant articles and documents

Two methods for the preparation of sitagliptin phosphate: Via chemical resolution and asymmetric hydrogenation

Two effective processes have been developed for the preparation of sitagliptin phosphate. The approach of chemical resolution obtained R-sitagliptin in five steps from commercially available starting materials using the inexpensive NaBH4 to reduce the enamine and then using (-)-di-p-toluoyl-l-tartaric acid to resolve racemates in 11% yield overall. The route successfully avoids the use of expensive noble metal as catalysts compared with traditional synthesis methods, resulting in greatly reduced costs and simplified synthetic routes. Other alternative asymmetric hydrogenation of β-ketomide routes for the synthesis of sitagliptin were found, two of the intermediates were synthesized for the first time. This journal is

PROCESSES FOR PREPARING 4-OXO-4-[3-(TRIFLUOROMETHYL)-5,6- DIHYDRO [L,2,41-TRIAZOLO[43-A]PYRAZIN-7(8H)-YL]-L-(2,4,5- TRIFLUOROPHENYL)BUTAN-2-AMINE

The present invention relates to synthesis of 4-oxo-4-[3-(trifluoromethyl)-5,6- dihydro [l,2,4]-triazolo[4,3-a]pyrazin-7(8H)-yl]-l-(2,4,5-trifluorophenyl)butan-2- amine of Formula (I) either in its racemic (R/S) form or any of its optically active (S) or (R) forms or enantiomeric excess mixture of any of the forms by novel processes. The invention further relates to certain novel intermediates useful in the preparation of compound of Formula (I) and processes for their preparation.

Process for the synthesis of beta-amino acids and derivatives thereof

The present invention relates to a process for the preparation of β-amino acids and derivatives thereof, which is especially suited for gliptins and particularly sitagliptin. A key step makes use of suitably derivatized epoxides or aziridines, which owing to a chirality provides a source of chirality for intermediates which are suitable for building up β-amino acids and similar compounds, in particular in the construction of the sitagliptin molecule.