Potassium ethanethioate → HCID 58595089, compound

HRID 891589Notes

Reaction equation

HRID 891589 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([N:9]2[CH2:13][CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10]2)[S:7][CH:8]=1)(=[O:3])[NH2:2].[C:19]([O-:22])(=[S:21])[CH3:20].[K+]>C(#N)C>[C:19]([S:21][C@@H:11]1[CH2:12][CH2:13][N:9]([C:6]2[S:7][CH:8]=[C:4]([C:1](=[O:3])[NH2:2])[N:5]=2)[CH2:10]1)(=[O:22])[CH3:20]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86590856HCID 86590856, compound

Product 1

HCID 58595089HCID 58595089, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3S)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (1.15 g) (obtained as described in Reference Example 20(8)) in acetonitrile (35 ml) was added potassium thioacetate (1.35 g, 11.8 mmol) at room temperature, and the mixture was heated under reflux for 6 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 sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate→2% methanol in ethyl acetate as the eluant to afford (3R)-3-acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)pyrrolidine (962 mg, yield 90%) as a pale brown solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customthe completion of the reaction
  4. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  5. washThe organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0043fd5a452249e6b2293cdcf656aa19
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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