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

HRID 1590494
ノート
印刷プレビュー

反応式

HRID 1590494 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3dca12d896bd482fad13e44e23b847d6
出典データセット
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05202437

反応ノート

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