1-(4-Allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → HCID 22242905, compound

HRID 891683Notes

Reaction equation

[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:15][CH:14](OS(C)(=O)=O)[CH2:13]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3].[C:21]([O-:24])(=[S:23])[CH3:22].[K+]>CN(C)C=O>[C:21]([S:23][CH:14]1[CH2:13][N:12]([C:9]2[S:10][CH:11]=[C:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[N:8]=2)[CH2:15]1)(=[O:24])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (2.70 g, 8.51 mmol) (obtained as described in Reference Example 41(3)) in dimethylformamide (135 ml) was added potassium thioacetate (5.83 g, 51.1 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 10 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with 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 n-hexane:ethyl acetate (2:1) as the eluant to afford 3-acetylthio-1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)azetidine (1.61 g, yield 63%) as a pale brown solid.

Workup

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

Sources & evidence

ORD record: ord-feef3a46e6f243c999c546b823ba711e
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001897B2

Reaction notes

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