HCID 15056137, compound → (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine

HRID 1650836Notes

Reaction equation

HRID 1650836 reaction equation
CS(O[C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([CH2:24][N:25]2[CH2:29][CH2:28][NH:27][C:26]2=[O:30])[CH2:7]1)(=O)=O.[C:31]([O-:34])(=[S:33])[CH3:32].[K+]>CN(C)C=O>[C:31]([S:33][C@@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[O:12])[C@H:8]([CH2:24][N:25]2[CH2:29][CH2:28][NH:27][C:26]2=[O:30])[CH2:7]1)(=[O:34])[CH3:32]

Participants

4

Reactant 2

HCID 15056137HCID 15056137, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 57168905(2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (1.84 g) in dimethylformamide (40 ml) was added potassium thioacetate (0.95 g) and the mixture was stirred at 70°-80° C. for 2 hours. The reaction mixture was poured into ice-water (200 ml) and extracted 3 times with ethyl acetate (100 ml). The extract 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 chloroform and methanol (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (1.23 g).

Workup

  1. extractionextracted 3 times with ethyl acetate (100 ml)
  2. washThe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (100 g)
  6. washeluting with a mixture of chloroform and methanol (9:1 V/V)
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-bb6900570abe4d3982615f3960a04c1e
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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