150802-86-1

Basic information

• Product Name: (1R)-1-<(2S)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol
• Synonyms: (1R)-1-<(2S)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol
• CAS NO: 150802-86-1
• Molecular Weight: 200.185
• Mol File: 150802-86-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1R)-1-<(2S)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1-<(2S)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol(150802-86-1)
• EPA Substance Registry System: (1R)-1-<(2S)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol(150802-86-1)

Safety Data

• Hazardous Substances Data: 150802-86-1(Hazardous Substances Data)

Upstream product

• 25596-24-1 trimethyloxosulfonium bromide 
• 126918-16-9 (R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-one 
• 832152-01-9 (2R,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol 
• 832151-94-7 (2S,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol 
• 127001-03-0 (2S)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone 
• 126918-33-0 (1S)-1-<(2R)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 126918-14-7 (2S)-2',4'-Difluoro-2-hydroxypropiophenone 
• 126918-15-8 (S)-2-(p-toluenesulfonyloxy)-2',4'-difluoropropiophenone 
• 138373-68-9 (2R,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-1-trimethylsilanyl-butan-2-ol 
• 126918-32-9 (2S)-3-(2,4-Difluorophenyl)-3-buten-2-ol 
• 138373-69-0 (1S)-1-<(2S)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 377078-82-5 [(1R)-1-[(2S)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] benzoate 
• 188645-03-6 {(1R)-1-[(2S)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl} 3,5-dinitrobenzoate 

Downstream Products

• 126918-36-3 [(1R)-1-[(2S)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]methanesulfonate 
• 135270-10-9 (2S,3S)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane 
• 377078-85-8 (2S,3R)-3-(2,2-diethoxyethyl)amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 377078-91-6 1-[(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-(1H,3H)-imidazolone 
• 377078-88-1 1-(2,2-diethoxyethyl)-1-[(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]urea 
• 135270-14-3 (R)-1-[(R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl methanesulfonate 
• 188645-07-0 2-[(1R,2R)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone 
• 188645-06-9 2-[(1S,2R)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone 
• 138373-69-0 (1S)-1-<(2S)-2-(2,4-difluorophenyl)-2-oxiranyl>ethanol 
• 188645-04-7 {(1S)-1-[(2S)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl} benzoate 
• 188645-05-8 Trifluoro-methanesulfonic acid (R)-1-[(S)-2-(2,4-difluoro-phenyl)-oxiranyl]-ethyl ester 
• 155432-64-7 2-[(1R,2S)-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 
• 155432-64-7 2-[(1S,2S)-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 HALOHYDRIN DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE EPOXY ALCOHOL DERIVATIVE FROM THE SAME

The present invention provides an industrially safe, easily operable process for producing an optically active epoxy alcohol derivative useful as an intermediate for pharmaceuticals from inexpensively available materials, and also provides a novel halohydrin derivative serving as an important intermediate for the epoxyalcohol derivative. Furthermore, the present invention provides a process for producing an intermediate for a triazole antifungal agent by allowing a halohydrin to react with a triazole sulfonamide, the process including a small number of steps. A process for producing an optically active epoxy alcohol derivative includes allowing an optically active α-substituted propionate derivative to react with a haloacetic acid derivative in the presence of a base to prepare an optically active haloketone derivative, allowing the resulting haloketone derivative to react with an aryl metal compound to stereoselectively prepare a halohydrin derivative, eliminating a substituent for the hydroxy group of the halohydrin derivative, and performing epoxidation with a base. Furthermore, a process for producing an intermediate for a triazole antifungal agent includes allowing a halohydrin derivative to react with a triazole sulfonamide, the process including a small number of steps.

Production methods of epoxytriazole derivative and intermediate therefor

An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base. wherein Ar is a phenyl group optionally substituted by 1 to 3 halogen atom(s) or trifluoromethyl group, R is a hydrogen atom or lower alkyl group, and X is a leaving group.

Optically active antifungal azoles. VII. Synthesis and antifungal activity of stereoisomers of 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 (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-tetrafluopropoxy)phenyl]-3(2H,4H)-1,2,4- triazolone [(1R,2R)-1: TAK-187] is a new antifungal agent selected as a candidate for clinical trials. The three stereoisomers [(1S,2S)-, (1R,2S)- and (1S,2R)-1] of this compound were prepared to clarify the relationship between the stereochemistry and the biological activities. In vitro and in vivo assays of antifungal activity revealed TAK-187 [(1R,2R)-1] is the most potent among the four stereoisomers. Furthermore, TAK-187 was found to exert a strong and selective inhibitory effect on the sterol synthesis in Candida albicans as compared with that in rat liver.