174563-18-9

Basic information

• Product Name: 2-<(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone
• Synonyms: 2-<(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone
• CAS NO: 174563-18-9
• Molecular Weight: 569.482
• Mol File: 174563-18-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-<(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-<(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone(174563-18-9)
• EPA Substance Registry System: 2-<(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone(174563-18-9)

Safety Data

• Hazardous Substances Data: 174563-18-9(Hazardous Substances Data)

Upstream product

• 174563-11-2 (2R)-2-[4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]propanoyl chloride 
• 174563-10-1 (2R)-2-<4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl>propanoic acid 
• 174563-08-7 (2S)-2',4'-difluoro-2-trifluoromethanesulfonyloxypropiophenone 
• 372-18-9 1,3-Difluorobenzene 
• 124-63-0 methanesulfonyl chloride 
• 174562-97-1 2-<(1R,2S)-2-(2,4-difluorophenyl)-2,3-dihydroxy-1-methylpropyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone 
• 174562-98-2 2-<(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-(isopropoxydimethylsilyl)-1-methylpropyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone 
• 174562-96-0 2-<(1R,2S)-2-(2,4-difluorophenyl)-2-formyl-2-hydroxy-1-methylethyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone 
• 174563-17-8 2-<(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone 
• 174563-09-8 benzyl (2R)-2-<4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl>propanoate 

Downstream Products

• 155432-64-7 2-<(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl>-4-<4-(2,2,3,3-tetrafluoropropoxy)phenyl>-3(2H,4H)-1,2,4-triazolone 

Relevant articles and documents

Optically active antifungal azoles. IX. An alternative synthetic route for 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol- 1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)1,2,4- triazolone and its analogs

A new route for the synthesis of the optically active antifungal azole TAK-187, 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4- triazol-1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoroptopoxy)phenyl]3(2H,4H)-1,2,4- triazolone, was established. The key synthetic intermediate, 2-[(1R)-2-(2,4- difluorophenyl)-2-oxo-1-methylethyl]-4-[4-(2,2,3,3- tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (8), was prepared starting from the esters (11a, b) of (S)-lactic acid in a stereocontrolled manner. This optically active propiophenone derivative 8 was converted to the one carbon-elongated (1R,2S)-diol 7, which was then reacted with 1H-1,2,4- triazole to yield TAK-187. This newly developed route was applied to the synthesis of the analogs (25a, b - 28a, b) containing an imidazolone or imidazolidinone nucleus.