Water → HCID 10154808, compound

A solution of Oxone (Trade Mark) (581 mg, 0.946 mmol) in water was added to a stirred suspension of the sulphide of Example 21 (200 mg, 0.63 mmol) in methanol (2.5 ml) at 0° C. producing a viscous white suspension. The cooling bath was removed and further methanol (2.5 ml) was added to aid dissolution and stirring. The mixture was stirred at room temperature for 2½ hours and at 50° C. for 24 hours. After cooling the mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (50 ml) and water (25 ml). The organic layer was washed with brine (25 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a white solid (195 mg). The crude product was pre-absorbed on silica gel and purified by flash chromatography on silica gel eluting with methanol:dichloromethane (2:98, by volume) to provide the title compound (175 mg) as a white solid, m.p. 199–200° C.

1. customproducing a viscous white suspension
2. customThe cooling bath was removed
3. additionfurther methanol (2.5 ml) was added to aid dissolution
4. stirringThe mixture was stirred at room temperature for 2½ hours and at 50° C. for 24 hours
5. temperatureAfter cooling the mixture
6. concentrationwas concentrated under reduced pressure
7. customthe residue was partitioned between dichloromethane (50 ml) and water (25 ml)
8. washThe organic layer was washed with brine (25 ml)
9. dry with materialdried over magnesium sulphate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-495554960de54f4981d7aef455e5bd6f

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141585B2