1-(4-Carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)azetidine

HRID 891555Notes

Reaction equation

HRID 891555 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)[S: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[S:7][CH:8]=[C:4]([C:1](=[O:3])[NH2:2])[N:5]=2)[CH2:12]1)(=[O:21])[CH3:19]

Participants

4

Reactant 2

HCID 222429891-(4-Carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

Product 1

HCID 222428523-Acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)azetidineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (3.04 g, 11.0 mmol) (obtained as described in Reference Example 3(3)) in dimethylformamide (152 ml) was added potassium thioacetate (7.5 g, 65.8 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 successively with saturated aqueous sodium hydrogencarbonate solution and 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→4% methanol in ethyl acetate as the eluant to afford 3-acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)azetidine (1.97 g, yield 70%) as a pale brown solid.

Workup

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-5857c53155824a2682e6748fe64956de
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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