Potassium ethanethioate → HCID 58595136, compound

HRID 891637Notes

Reaction equation

HRID 891637 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:13][C:14]([C:16]1[N:17]=[C:18]([N:21]2[CH2:24][CH:23](OS(C)(=O)=O)[CH2:22]2)[S:19][CH:20]=1)=[O:15])[CH2:11][CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30]([O-:33])(=[S:32])[CH3:31].[K+]>CN(C)C=O>[C:30]([S:32][CH:23]1[CH2:22][N:21]([C:18]2[S:19][CH:20]=[C:16]([C:14](=[O:15])[NH:13][C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[CH2:11][CH3:12])[N:17]=2)[CH2:24]1)(=[O:33])[CH3:31]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 87884665HCID 87884665, compound

Product 1

HCID 58595136HCID 58595136, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-{4-[(1S)-1-(t-butyldimethylsilyloxymethyl)propylcarbamoyl]-1,3-thiazol-2-yl}-3-methanesulfonyloxyazetidine (1.02 g, 2.20 mmol) (obtained as described in Reference Example 34(5)) in dimethylformamide (50 ml) was added potassium thioacetate (1.51 mg, 13.2 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) overnight. 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 sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (4:1→2:1) as the eluant to afford 3-acetylthio-1-{4-[(1S)-1-(t-butyldimethylsilyloxymethyl)propylcarbamoyl]-1,3-thiazol-2-yl}azetidine (618 mg, yield 63%) as a pale brown oil.

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 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-b4538ecb07dc43c780abe3607944d53d
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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