Acetonitrile → (2S,4S)-2-(2,5-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

HRID 1590494Notes

Reaction equation

HRID 1590494 reaction equation
ClCC(N[C@:6]1([CH3:44])[CH2:10][C@H:9]([S:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][N:7]1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:32])=O.[O-:45][C:46]#[N:47].[K+].[C:49]([O:52]CC)(=O)[CH3:50].C(#[N:57])C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:45]=[C:46]1[NH:57][CH2:50][C:49](=[O:52])[N:47]1[CH2:44][C@@H:6]1[CH2:10][C@H:9]([S:11][C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8][N:7]1[C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=1)=[O:32]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 11378442Potassium cyanateHCID 67856618(2S,4S)-2-(chloroacetylamino)-methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)-pyrrolidine

Product 1

HCID 15056149(2S,4S)-2-(2,5-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

A solution of (2S,4S)-2-(chloroacetylamino)-methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)-pyrrolidine (1.0 g), potassium cyanate (1.3 g) and tetra-n-butylammonium iodide (0.2 g) in acetonitrile (50 ml) was stirred at 60°-80° C. for 8 hours. To a reaction mixture was added ethyl acetate (150 ml) and the organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The resalting residue was chromatographed on silica gel (50 g) eluting with a mixture of chloroform and acetone (9:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-(2,5-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (0.82 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe resalting residue was chromatographed on silica gel (50 g)
  6. washeluting with a mixture of chloroform and acetone (9:1, V/V)
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3dca12d896bd482fad13e44e23b847d6
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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