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

HRID 1590494
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HRID 1590494 반응식
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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매

1
HCID 67553Tetrabutylammonium Iodide촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3dca12d896bd482fad13e44e23b847d6
출처 데이터셋
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05202437

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