1-(4-Ethoxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:14][CH:13](OS(C)(=O)=O)[CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[C:20]([O-:23])(=[S:22])[CH3:21].[K+]>CN(C)C=O>[C:20]([S:22][CH:13]1[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)[CH2:14]1)(=[O:23])[CH3:21]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (742 mg, 2.42 mmol) (obtained as described in Reference Example 1(3)) in dimethylformamide (37 ml) was added potassium thioacetate (1.11 g, 9.72 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 6 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 residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1) as the eluant to afford 3-acetylthio-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine (494 mg, yield 71%) as a pale brown solid.
Workup
- customat room temperature
- 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 residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-243ab416492349908bf9c2bbef66f1b7
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07001897B2
Reaction notes
Loading…