Potassium ethanethioate → 4-Acetylthio-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)piperidine
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14](OS(C)(=O)=O)[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[C:22]([O-:25])(=[S:24])[CH3:23].[K+]>CN(C)C=O>[C:22]([S:24][CH:14]1[CH2:13][CH2:12][N:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:16][CH2:15]1)(=[O:25])[CH3:23]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-4-methanesulfonyloxypiperidine (76 mg, 0.23 mmol) (obtained as described in Reference Example 13(3)) in dimethylformamide (4.0 ml) was added potassium thioacetate (145 mg, 1.3 mmol) at room temperature, and the reaction mixture was then stirred in an oil bath (80° C.) for 8 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1) as the eluant to afford 4-acetylthio-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)piperidine (67 mg, yield 94%) as a pale brown solid.
Workup
- customthe completion of the reaction
- customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
- washThe organic layer was washed with saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-409c6842269d4bccbb06a26eb48083f7
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07001897B2
Reaction notes
Loading…