1-(4-Cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-(4-cyano-1,3-thiazol-2-yl)azetidine

HRID 891559Notes

Reaction equation

[C:1]([C:3]1[N:4]=[C:5]([N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[S:6][CH:7]=1)#[N:2].[C:17]([O-:20])(=[S:19])[CH3:18].[K+]>CN(C)C=O>[C:17]([S:19][CH:10]1[CH2:9][N:8]([C:5]2[S:6][CH:7]=[C:3]([C:1]#[N:2])[N:4]=2)[CH2:11]1)(=[O:20])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(4-cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (1.12 g, 4.32 mmol) (obtained as described in Reference Example 4(3)) in dimethylformamide (56 ml) was added potassium thioacetate (3.89 g, 27.0 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 4 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 (2:1) as the eluant to afford 3-acetylthio-1-(4-cyano-1,3-thiazol-2-yl)azetidine (0.767 g, yield 75%) 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-7636154b1bb844689a3a1973adb8e4fe
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001897B2

Reaction notes

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