HCID 22242831, compound → HCID 22242846, compound
Reaction equation
[C:1]([C:4]1[N:5]=[C:6]([N:9]2[CH2:12][CH:11](OS(C)(=O)=O)[CH2:10]2)[O:7][CH:8]=1)(=[O:3])[NH2:2].[C:18]([O-:21])(=[S:20])[CH3:19].[K+]>CN(C)C=O>[C:18]([S:20][CH:11]1[CH2:10][N:9]([C:6]2[O:7][CH:8]=[C:4]([C:1](=[O:3])[NH2:2])[N:5]=2)[CH2:12]1)(=[O:21])[CH3:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-(4-carbamoyl-1,3-oxazol-2-yl)-3-methanesulfonyloxyazetidine (469 mg, 1.80 mmol) (obtained as described in Reference Example 22(3)) in dimethylformamide (23 ml) was added potassium thioacetate (1.23 g, 10.80 mmol) at room temperature, and the mixture was 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 residue was purified by chromatography on a silica gel column using ethyl acetate: methanol (10:1) as the eluant to afford 3-acetylthio-1-(4-carbamoyl-1,3-oxazol-2-yl)azetidine (275 mg, yield 63%) as a white 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 residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-148a6ec0aec54b34b9a5e449526787dc
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07001897B2
Reaction notes
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