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Potassium Carbonate → 4-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

HRID 52884
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HRID 52884 반응식
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.[C:28]([C:31]1[N:32]=[C:33]([CH2:38][CH2:39][CH2:40][CH3:41])[NH:34][C:35]=1[C:36]#[N:37])(=[O:30])[CH3:29]>CN(C)C(=O)C.C(OCC)(=O)C>[C:28]([C:31]1[N:32]=[C:33]([CH2:38][CH2:39][CH2:40][CH3:41])[N:34]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:11][CH:10]=2)[C:35]=1[C:36]#[N:37])(=[O:30])[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178441657HCID 178441657, 화합물

생성물 1

HCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole수율 45.6%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매
HCID 31374
Dimethylacetamide
용매

실험 절차

0.87 g of potassium carbonate and 2.4 g of t-butyl 4'-bromomethylbiphenyl-2-carboxylate were added to a solution of 1.2 g of 4-acetyl-2-butyl-5-cyanoimidazole (prepared as described in Preparation 5) in 12 ml of N,N-dimethylacetamide, and the resulting mixture was shirred at room temperature for 3 hours. At the end of this time, the reaction mixture was diluted with 100 ml of ethyl acetate and washed with a saturated aqueous solution of sodium chloride. The aqueous layer was once again extracted with 50 ml of ethyl acetate, and the combined extracts were washed with a saturated aqueous solution of sodium chloride. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.31 g of the title compound.

후처리

  1. washwashed with a saturated aqueous solution of sodium chloride
  2. extractionThe aqueous layer was once again extracted with 50 ml of ethyl acetate
  3. washthe combined extracts were washed with a saturated aqueous solution of sodium chloride
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-d033052598804b7d976daa0bbd288f27
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05616599

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