Potassium ethanethioate → HCID 58595171, compound

HRID 891581Notes

Reaction equation

HRID 891581 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 86590853HCID 86590853, compound

Product 1

HCID 58595171HCID 58595171, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R)-1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (190 mg, 0.652 mmol) (obtained as described in Reference Example 18(7)) in acetonitrile (6 ml) was added potassium thioacetate (223 mg, 1.96 mmol) at room temperature. The mixture was heated under reflux 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 sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1)→ethyl acetate→2% methanol in ethyl acetate as the eluant to afford (3S)-3-acetylthio-1-(4-carbamoyl-1,3-thiazol-2-yl)pyrrolidine (135 mg, yield 77%) as a pale brown solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 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-b77a129665fe473190cd33a4c393a92b
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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