Thioacetic acid → (2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine

HRID 1590488Notes

Reaction equation

HRID 1590488 reaction equation
[H-].[Na+].[C:3]([SH:6])(=[O:5])[CH3:4].CS(O[C@H:12]1[CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C@H:14]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([CH3:36])[C:32]2=[O:37])[CH2:13]1)(=O)=O>CN(C)C=O>[C:3]([S:6][C@@H:12]1[CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:18])[C@H:14]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([CH3:36])[C:32]2=[O:37])[CH2:13]1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 10484Thioacetic acidHCID 24758Sodium hydrideHCID 15056144HCID 15056144, compound

Product 1

HCID 15056145(2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of sodium hydride (0.35 g) in N,N-dimethylformamide (30 ml) was added dropwise thioacetic S-acid (0.74 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. A solution of (2S,4R)-4-methanesulfonyloxy-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine (3.17 g) in N,N-dimethylformamide (7 ml) was added to the mixture obtained above with stirring at the same temperature. The mixture was stirred at 80°-90° C. for 2 hours. The reaction mixture was poured into ice-water (100 ml) and extracted twice 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 (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4 -nitrobenzyloxycarbonyl)pyrrolidine (1.74 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. customobtained above
  4. stirringwith stirring at the same temperature
  5. stirringThe mixture was stirred at 80°-90° C. for 2 hours
  6. extractionextracted twice with ethyl acetate (100 ml)
  7. washThe extract was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe resulting residue was chromatographed on silica gel (100 g)
  11. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  12. additionThe fractions containing the desired compound
  13. customwere collected
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-2ea3ea1941904c87b347e26106d0fce9
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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