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Acetone → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxyethyl)imidazole-5-carbonitrile

HRID 52920
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HRID 52920 반응식
[BH4-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH2:33][CH2:34][CH2:35][CH3:36])[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:16][CH:15]=2)[C:10]=1[C:11]#[N:12])(=[O:5])[CH3:4].CC(C)=O>C(O)C>[C:29]([O:28][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:9]2[C:10]([C:11]#[N:12])=[C:6]([CH:3]([OH:5])[CH3:4])[N:7]=[C:8]2[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:15][CH:16]=1)=[O:27])([CH3:32])([CH3:31])[CH3:30]
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참가 물질

5

반응물 3

HCID 180AcetoneHCID 4311764Sodium borohydride2회HCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

생성물 1

HCID 190362351-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxyethyl)imidazole-5-carbonitrile수율 99.6%

시약·촉매·용매 1

HCID 702Ethanol
용매

실험 절차

0.098 g of sodium borohydride was added to a solution of 1.18 g of 4-acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butylimidazole-5-carbonitrile [prepared as described in step (a) above] in 30 ml of ethanol, and the resulting mixture was stirred at room temperature for 1 hour. The excess sodium borohydride was decomposed by adding acetone, and then the reaction mixture was concentrated by evaporation under reduced pressure. The residue was diluted with an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was dried and concentrated by evaporation under reduced pressure. The oily residue was purified by column chromatography through silica gel, using a 3:2 by volume mixture of ethyl acetate and hexane as the eluent, to afford 1.18 g of the title compound as a viscous oil.

후처리

  1. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
  2. additionThe residue was diluted with an aqueous solution of sodium chloride
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe oily residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and hexane as the eluent

출처 및 근거

ORD 기록
ord-03392fbbd4a347f9bfe4f71b3badbc66
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05616599

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