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Ethyl Acetate → Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-ethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate

HRID 265100
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HRID 265100 반응식
CC(C)([O-])C.[K+].[CH2:7]([C:9]1[NH:10][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([C:14]([OH:17])([CH3:16])[CH3:15])[N:13]=1)[CH3:8].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:26]=1.C(OCC)(=O)C>CN(C)C(=O)C.O>[C:40]([O:39][C:37]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:10]2[C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([C:14]([OH:17])([CH3:16])[CH3:15])[N:13]=[C:9]2[CH2:7][CH3:8])=[CH:26][CH:27]=1)=[O:38])([CH3:43])([CH3:42])[CH3:41]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 178470390HCID 178470390, 화합물

생성물 1

HCID 10672775Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-ethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate수율 89.5%

시약·촉매·용매 2

HCID 962Water용매
HCID 31374Dimethylacetamide용매

실험 절차

0.337 g of potassium t-butoxide was added to a solution of 0.68 g of ethyl 2-ethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate (prepared as described in Preparation 37) in 7 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 10 minutes. 1.04 g of t-butyl 4'-bromomethylbiphenyl-2-carboxylate was then added to the resulting solution, and the reaction mixture was stirred at room temperature for 4 hours. At the end of this time, it was mixed with ethyl acetate and water. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 1.32 g of the title compound as a gum.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 4 hours
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

출처 및 근거

ORD 기록
ord-590b028f915d42a58dff5dc7bafec378
출처 데이터셋
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05646171

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