Dimethyl Sulfoxide → HCID 76576892, compound

Temperature

-78 °C

A solution containing oxalyl chloride (5.45 mL) in dichloromethane (130 mL) was cooled to −78° C. under a nitrogen atmosphere. A solution containing dimethyl sulfoxide (4.85 mL) in dichloromethane (5 mL) was added dropwise to the reaction solution at the same temperature. After stirring at the same temperature for 10 minutes, a solution containing 3-allyloxy-propan-1-ol (4.99 g) in dichloromethane (5 mL) was added dropwise to the reaction solution. After stirring at the same temperature for one hour, triethylamine (20.4 mL) was added to the reaction solution. The cooling bath was removed. The reaction solution was warmed to room temperature and stirred at room temperature for one hour. Saturated aqueous ammonium chloride was added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (100 mL) and water (10 mL). Sodium acetate (12 g) and hydroxylamine sulfate (8.02 g) were added to the reaction solution at room temperature. The reaction solution was stirred at room temperature for 15 hours. Then, a saturated sodium chloride solution and ethyl acetate were added and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride again. The organic layer was dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (5.5 g).

1. additionwas added dropwise to the reaction solution at the same temperature
2. additionwas added dropwise to the reaction solution
3. stirringAfter stirring at the same temperature for one hour
4. customThe cooling bath was removed
5. temperatureThe reaction solution was warmed to room temperature
6. stirringstirred at room temperature for one hour
7. additionSaturated aqueous ammonium chloride was added to the reaction solution
8. customthe organic layer was separated
9. washThe organic layer was washed with saturated aqueous sodium chloride
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe insoluble matter was separated by filtration
12. concentrationthe filtrate was concentrated under reduced pressure
13. dissolutionThe residue was dissolved in ethanol (100 mL)
14. additionSodium acetate (12 g) and hydroxylamine sulfate (8.02 g) were added to the reaction solution at room temperature
15. stirringThe reaction solution was stirred at room temperature for 15 hours
16. additionThen, a saturated sodium chloride solution and ethyl acetate were added
17. customthe organic layer was separated
18. washThe organic layer was washed with saturated aqueous sodium chloride again
19. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
20. customThe insoluble matter was separated by filtration
21. concentrationthe filtrate was concentrated under reduced pressure
22. customThe residue was purified by silica gel column chromatography

ORD record

ord-04c7988671eb4d0588542647de03038a

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158620B2