1H-1,2,4-Triazole → (2R,3R)-2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol

Temperature

70 °C

1,2,4-Triazole (7 mg; 0.1 mmol) is dissolved in DMF (0.5 ml). Sodium hydride (4.4 mg; 60% suspension in paraffin; 0.1 mmol) is added and the reaction mixture is heated to 70° C. for one hour. The reaction mixture is cooled to room temperature and 1(S)-[2(S)-(2,5-Difluoro-phenyl)-oxiranyl]-ethanol (5 mg; 0.025 mmol from example 8) dissolved in DMF (0.5 ml) is added slowly. The reaction mixture is then heated to 70° C. for three hours. The solvent is evaporated. The residue is taken-up in ethyl acetate (5 ml) and water (3 ml). The phases are separated. The aqueous layer is extracted 3 times with ethyl acetate (3 times 5 ml). The combined organic phases are washed twice with water (2 times 5 ml). The organic phase is dried over sodium sulfate. The solids are filtered off and the solvent is removed under reduced pressure. 5 mg of (2R,3R)-2-(2,5-Difluoro-phenyl)-1-[1,2,4]-triazol-1-yl-butane-2,3-diol are obtained as a light yellow oil.

1. temperatureThe reaction mixture is cooled to room temperature
2. additionis added slowly
3. temperatureThe reaction mixture is then heated to 70° C. for three hours
4. customThe solvent is evaporated
5. customThe phases are separated
6. extractionThe aqueous layer is extracted 3 times with ethyl acetate (3 times 5 ml)
7. washThe combined organic phases are washed twice with water (2 times 5 ml)
8. dry with materialThe organic phase is dried over sodium sulfate
9. filtrationThe solids are filtered off
10. customthe solvent is removed under reduced pressure

ORD record

ord-141c2ce43c7c41149243040d3243650a

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076494B2