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

HRID 1650847
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HRID 1650847 반응식
Cl[CH2:2][C:3]([NH:5][CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])=[O:4].[O-:45][C:46]#[N:47].[K+].C(OCC)(=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[O:45]=[C:46]1[NH:47][CH2:2][C:3](=[O:4])[N:5]1[CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33]
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참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 11378442Potassium cyanateHCID 57097948(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)pyrrolidine수율 81.2%

시약·촉매·용매 2

HCID 67553
Tetrabutylammonium Iodide
촉매
HCID 6342Acetonitrile용매

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 resulting 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 resulting 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-461681f03dbb4b409ed760d3ef672ba1
출처 데이터셋
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04925838

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