Hydrogen Peroxide → HCID 18358034, compound

500 mg of N-[5-(1,2-dithiolan-3-yl)pentanoyl]methanesulfonamide (prepared as described in Example 2) were dissolved in 10 ml of acetone, and 0.44 ml of a 31% w/v aqueous solution of hydrogen peroxide was added to the solution, whilst ice-cooling. The mixture was stirred and then left to stand at room temperature overnight. At the end of this time, a further 0.2 ml of a 31% w/v aqueous solution of hydrogen peroxide was added to the reaction mixture, and then the mixture was stirred at room temperature for 30 minutes, and then stirred on an oil bath at 50° C. for 1 hour. The mixture was then left to stand at room temperature for 3 days, after which it was stirred on an oil bath at 50° C. for 10 hours; it was then left to stand at room temperature overnight. The solvent was then removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue thus obtained, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then the solvent was removed by evaporation under reduced pressure. The residue thus obtained was purified by reverse phase preparative silica gel column chromatography, using 1:3 and 2:3 by volume mixtures of acetonitrile and water as the eluent. The solvent was evaporated from the eluted fraction thus obtained under reduced pressure, and the fraction was lyophilised, to obtain 0.15 g of the title compound (diastereomer mixture) as a colorless oil having an Rf value of 0.43 (silica gel thin layer chromatography, using a 10:1 by volume mixture of ethyl acetate and methanol as the developing solvent).

1. temperaturecooling
2. waitleft
3. stirringthe mixture was stirred at room temperature for 30 minutes
4. stirringstirred on an oil bath at 50° C. for 1 hour
5. waitThe mixture was then left
6. waitto stand at room temperature for 3 days
7. stirringafter which it was stirred on an oil bath at 50° C. for 10 hours
8. waitit was then left
9. waitto stand at room temperature overnight
10. customThe solvent was then removed from the reaction mixture by evaporation under reduced pressure, and water
11. additionwas added to the residue
12. customthus obtained
13. extractionafter which it was extracted with ethyl acetate
14. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
15. dry with materialdried over anhydrous sodium sulfate
16. customthe solvent was removed by evaporation under reduced pressure
17. customThe residue thus obtained
18. customwas purified by reverse phase preparative silica gel column chromatography
19. customThe solvent was evaporated from the eluted fraction
20. customthus obtained under reduced pressure

ORD record

ord-c5b61ea20e9d4ed5b4a110b9c9dd75a4

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06013663