Sodium Chloride → HCID 18652163, compound

HRID 1586750Notes

Reaction equation

HRID 1586750 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][C@H:8]1[CH2:17][N:18]1[C:25]2[N:21]([N:22]=[CH:23][CH:24]=2)[CH:20]=[CH:19]1)=[O:6])[CH:2]=[CH2:3].[C:26]([O-:29])(=[S:28])[CH3:27].[K+].C(OCC)(=O)C.[Cl-].[Na+]>C(#N)C>[C:26]([S:28][C@@H:10]1[CH2:11][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C@H:8]([CH2:17][N:18]2[C:25]3[N:21]([N:22]=[CH:23][CH:24]=3)[CH:20]=[CH:19]2)[CH2:9]1)(=[O:29])[CH3:27]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 18652161HCID 18652161, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 18652163HCID 18652163, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2S,4R)-1-allyloxycarbonyl-2-(imidazo [1,2-b]pyrazol-1-yl)methyl-4-methanesulfonyloxypyrrolidine (3.04 g) and potassium thioacetate (1.41 g) in acetonitrile (60 ml) was stirred under refluxing for 4 hours. To the reaction mixture were added ethyl acetate (100 ml) and aqueous sodium chloride (50 ml) with stirring and then the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of dichloromethane and acetone (5:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-acetylthio-1-allyloxycarbonyl -2-(imidazo[1,2-b]pyrazol-1-yl)methylpyrrolidine (2.33 g).

Workup

  1. temperatureunder refluxing for 4 hours
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe resulting residue was chromatographed on silica gel (100 g)
  7. washeluting with a mixture of dichloromethane and acetone (5:1, V/V)
  8. additionThe fractions containing the desired compound
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-56074909183b4682a1c500efc65e4779
Source dataset
uspto-grants-1993_06
Patent number
US05215983

Reaction notes

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