Potassium ethanethioate → HCID 58595079, compound

HRID 891582Notes

Reaction equation

HRID 891582 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([N:8]2[CH2:12][CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9]2)[S:6][CH:7]=1)#[N:2].[C:18]([O-:21])(=[S:20])[CH3:19].[K+]>C(#N)C>[C:18]([S:20][C@H:10]1[CH2:11][CH2:12][N:8]([C:5]2[S:6][CH:7]=[C:3]([C:1]#[N:2])[N:4]=2)[CH2:9]1)(=[O:21])[CH3:19]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86590854HCID 86590854, compound

Product 1

HCID 58595079HCID 58595079, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R)-1-(4-cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxypyrrolidine (300 mg, 1.10 mmol) (obtained as described in Reference Example 18(7)) in acetonitrile (9 ml) was added potassium thioacetate (376 mg, 3.30 mmol) at room temperature. The mixture was heated under reflux for 5 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 (5:1→1:1) as the eluant to afford (3S)-3-acetylthio-1-(4-cyano-1,3-thiazol-2-yl)pyrrolidine (137 mg, yield 50%) as a pale brown solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 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-d863a3fc39904887b1a83c0fbc3a5f46
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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