Water → HCID 68487391, compound

Temperature

60 °C

To a mixed solution of THF (20 mL) and water (10 mL) containing 4-(azidomethyl)-6-chloro-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one (2.59 g, 8.44 mmol), trimethyl phosphite (2 mL, 16.9 mmol) was added at room temperature, and the reaction solution was stirred at 60° C. for 5 hours. After the reaction solution was left to cool, water was added thereto, and the resulting solution was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. To the residue, a 4 N hydrochloric acid-dioxane solution (30 mL) was added, and the mixture was stirred at 40° C. for 24 hours. After the mixture was left to cool, the resulting solid was collected by filtration and washed with ethyl acetate and then dried under reduced pressure, whereby the objective compound (2.31 g, 86%) was obtained as a white solid.

1. additionwas added at room temperature
2. waitAfter the reaction solution was left
3. temperatureto cool
4. customthe organic layer was separated
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. customAfter the drying agent was removed by filtration
8. customthe solvent was evaporated under reduced pressure
9. additionTo the residue, a 4 N hydrochloric acid-dioxane solution (30 mL) was added
10. stirringthe mixture was stirred at 40° C. for 24 hours
11. waitAfter the mixture was left
12. temperatureto cool
13. filtrationthe resulting solid was collected by filtration
14. washwashed with ethyl acetate
15. dry with materialdried under reduced pressure, whereby the objective compound (2.31 g, 86%)
16. customwas obtained as a white solid

ORD record

ord-521b6b9be4d04f15af6e23e08559bc97

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314094B2