1-[4-(Benzenesulfonylamino)methyl-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]azetidine

HRID 891782Notes

Reaction equation

HRID 891782 reaction equation
[C:1]1([S:7]([NH:10][CH2:11][C:12]2[N:13]=[C:14]([N:17]3[CH2:20][CH:19](OS(C)(=O)=O)[CH2:18]3)[S:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([O-:29])(=[S:28])[CH3:27].[K+]>CN(C)C=O>[C:26]([S:28][CH:19]1[CH2:18][N:17]([C:14]2[S:15][CH:16]=[C:12]([CH2:11][NH:10][S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])[N:13]=2)[CH2:20]1)(=[O:29])[CH3:27]

Participants

4

Reactant 2

HCID 222428211-[4-(Benzenesulfonylamino)methyl-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

Product 1

HCID 222428723-Acetylthio-1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]azetidineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine (1.16 g, 2.98 mmol) (obtained as described in Reference Example 65(3)) in dimethylformamide (35 ml) was added potassium thioacetate (2.04 g, 17.9 mmol) at room temperature, and the mixture was stirred in an oil bath (90° C.) for 4 hours. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and 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 methylene chloride:ethyl acetate (5:1) as the eluant to afford 3-acetylthio-1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]azetidine (1.00 g, yield 91%) as a pale brown solid.

Workup

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium 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-27e46253c7074e1cbdf376e55c869617
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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