1352613-29-6

Basic information

• Product Name: (S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate
• Synonyms: (S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate
• CAS NO: 1352613-29-6
• Molecular Weight: 262.229
• Mol File: 1352613-29-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate(1352613-29-6)
• EPA Substance Registry System: (S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate(1352613-29-6)

Safety Data

• Hazardous Substances Data: 1352613-29-6(Hazardous Substances Data)

Upstream product

• 165047-24-5 2,4,5-trifluorobenzaldehyde 
• 17533-08-3 1-iodo-2,4,5-trifluorobenzene 
• 1365321-55-6 (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol 
• 955403-59-5 3-(2,4,5-trifluorophenyl)propanal 
• 64-17-5 ethanol 
• 868071-17-4 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid 
• 1246960-15-5 (S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol 
• 1283096-74-1 (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile 
• 327-52-6 1-bromo-2,4,5-trifluorobenzene 

Downstream Products

• 1352613-32-1 ethyl (S)-3-methansulfonyloxy-4-(2,4,5-trifluorophenyl)butyrate 
• 486460-32-6 sitagliptin 
• 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 
• 868071-17-4 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid 
• 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 
• 1352613-33-2 ethyl (R)-3-azido-4-(2,4,5-trifluorophenyl)butyrate 
• 1352613-36-5 (S)-3-hydroxy-N-methoxy-4-(2,4,5-trifluorophenyl)butanamide 
• 1256815-04-9 N-benzyloxy-4-(2,4,5-trifluorophenyl)-3(S)-hydroxybutanamide 
• 1352613-37-6 (S)-4-(methoxyamino)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl methane-sulfonate 
• 1352613-38-7 (S)-4-(benzyloxyamino)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl methanesulfonate 
• 1352613-39-8 (R)-1-methoxy-4-(2,4,5-trifluorobenzyl)azetidin-2-one 
• 1352613-40-1 (R)-3-(methoxyamino)-4-(2,4,5-trifluorophenyl)butanoic acid 
• 1352613-41-2 (R)-3-(methoxyamino)-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 (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 

Relevant articles and documents

A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method

Synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by the Sharpless asymmetric epoxidation reaction has been achieved. 2,4,5-Trifluorobenzaldehyde with methyl 2-(triphenyl-λ5-phosphanylidene)acetate gave methyl (E)-3-(2,4,5-trifluorophenyl)acrylate in 83% yield. The reduction of ester group with DibalH followed by Sharpless asymmetric epoxidation gave ((2R,3R)-3-(2,4,5-trifluorophenyl)oxiran-2-yl)methanol. Pd/C-catalyzed hydrogenation of epoxy alcohol furnished (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >90% ee and 71% yield.

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.