1807913-50-3

Basic information

• Product Name: 2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE
• Synonyms: FOSFLUCONAZOLE;FosflucozoleImpurity4;Fosfluconazole Impurity 4;FLUCONAZOLE DIHYDROGEN PHOSPHATE;2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE;2-(2,4-Difluorophenyl)-1,3-di(1h-1,2,4-triazol-1-yl)propan-2-yl hydrogen phosphonate;Phosphonic acid, mono[1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-(1H-1,2,4-triazol-1-ylmethyl)ethyl] ester
• CAS NO: 1807913-50-3
• Molecular Formula: C13H13F2N6O3P
• Molecular Weight: 370.25
• Mol File: 1807913-50-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE(1807913-50-3)
• EPA Substance Registry System: 2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE(1807913-50-3)

Safety Data

• Hazardous Substances Data: 1807913-50-3(Hazardous Substances Data)

Usage

Synthesis

The disclosed manufacturing route of synthesis utilized fluconazole (96) as a precursor and was prepared in two steps using inexpensive starting materials. Fluconazole was dissolved in dichloromethane with pyridine and was treated sequentially with phosphorus trichloride at –13°C and reacted at 13°C for 2 hr followed by an addition of benzyl alcohol at 14-16°C and reacted for 2 hrs at 10-15°C. The mixture was then cooled to 0°C and 30% hydrogen peroxide was added over three hours, maintaining the temperature below 20°C. After stirring the reaction at 20°C for 1hr, the intermediate 97 was isolated in 66% yield. Hydrogenation of the benzyl phosphate at 60 psi in water with 5% palladium on carbon gave the desired phosphate prodrug, fosfluconazole (XI) in 88% yield.