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Dichloromethane → 1-carbobenzyloxy-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl) ethyl)-3-phenylpyrrolidine

HRID 637103
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HRID 637103 반응식
[C:1]([N:11]1[CH2:15][CH2:14][C:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:16][CH2:17]OS(C)(=O)=O)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].I.[CH2:30]([O:32][CH2:33][CH2:34][N:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[C:36]1[N:44]1[CH2:50][CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)[CH3:31].C(N(CC)C(C)C)(C)C.ClCCl>C(#N)C.CO.ClCCl.C(OCC)(=O)C>[C:1]([N:11]1[CH2:15][CH2:14][C:13]([CH2:16][CH2:17][N:47]2[CH2:48][CH2:49][CH2:50][N:44]([C:36]3[N:35]([CH2:34][CH2:33][O:32][CH2:30][CH3:31])[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=4[N:37]=3)[CH2:45][CH2:46]2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]
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참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 184651041-Carbobenzyloxy-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidineHCID 865838874-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl) [1,4]diazepane hydriodic acid salt

생성물 1

HCID 184648341-carbobenzyloxy-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl) ethyl)-3-phenylpyrrolidine

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매HCID 21226129Dichloromethane methanol용매

실험 절차

Alternately, combine 1-carbobenzyloxy-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (5.7 g, 14.1 mmol), 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (7.52 g, 213.8 mmol), and N,N-diisopropylethylamine (9.6 mL, 55 mmol) in acetonitrile (200 mL). Heat to reflux. After 18 hours, evaporate in vacuo to give a residue. Combine the residue and dichloromethane. Extract twice with saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate and then 5% methanol/dichloromethane to give 1-carbobenzyloxy-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl)ethyl)-3-phenylpyrrolidine: Rf=0.38 (silica gel, 5% methanol/dichloromethane).

후처리

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. customto give a residue
  4. extractionExtract twice with saturated aqueous sodium bicarbonate solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give residue

출처 및 근거

ORD 기록
ord-07667c628c674a81996735f48fe549e5
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06194406B1

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