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Methyl iodide → Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(methoxymethyl)imidazole-5-carboxylate

HRID 265026
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 265026
[H-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([C:32]([O:34][CH3:35])=O)[N:25]=[C:24]2[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:18][CH:17]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].IC.C(OCC)(=O)C>CN(C)C(=O)C.O>[C:3]([O:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([CH2:32][O:34][CH3:35])[N:25]=[C:24]2[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:18][CH:17]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]
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Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 19036225Dimethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butylimidazole-4,5-dicarboxylate

Produkt 1

HCID 19036253Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(methoxymethyl)imidazole-5-carboxylateAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

0.057 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added to a solution of 0.478 g of methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate (prepared as described in Example 1) in 5 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, 0.125 ml of iodomethane were added, and the reaction mixture was stirred at 50° C. for 3 hours. The reaction mixture was then mixed with ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate; the solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and methylene chloride as the eluent, to give 0.30 g of the title compound as a gum.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 50° C. for 3 hours
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then removed by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and methylene chloride as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-eea410db976c4d76aaeb17d6808c0481
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05646171

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