3-Methanesulfonyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine → 3-Acetylthio-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

To a solution of 3-methanesulfonyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (400 mg, 1.21 mmol) (obtained as described in Reference Example 72(3)) in dimethylformamide (20 ml) was added potassium thioacetate (827 mg, 7.24 mmol) at room temperature and was stirred in an oil bath (80° C.) for 6 hours. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate→ethyl acetate:methanol (95:5) as the eluant to afford 3-acetylthio-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (266 mg, yield 71%) as a pale brown solid.

1. customthe completion of the reaction
2. customthe mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
3. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on a silica gel column

ORD-Eintrag

ord-0b288ee9ffd2480f883eceb1e81f4656

Quelldatensatz

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07001897B2