Ethyl Acetate → HCID 178440076, Verbindung

HRID 265178

Reaktionsgleichung

Reaktionsgleichung von HRID 265178
C(N(CC)C(C)C)(C)C.[OH:10][C:11]([C:14]1[N:15]=[C:16]([CH2:22][CH2:23][CH3:24])[NH:17][C:18]=1[C:19]([OH:21])=[O:20])([CH3:13])[CH3:12].[CH3:25][C:26]1[O:30][C:29](=[O:31])[O:28][C:27]=1[CH2:32]Cl.C(OCC)(=O)C>CN(C)C(=O)C.O>[OH:10][C:11]([C:14]1[N:15]=[C:16]([CH2:22][CH2:23][CH3:24])[NH:17][C:18]=1[C:19]([O:21][CH2:32][C:27]1[O:28][C:29](=[O:31])[O:30][C:26]=1[CH3:25])=[O:20])([CH3:13])[CH3:12]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-oneHCID 178440085HCID 178440085, Verbindung

Produkt 1

HCID 178440076HCID 178440076, VerbindungAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

1.76 ml of N,N-diisopropylethylamine were added to a suspension of 1.06 g of 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid [prepared as described in Preparation 22(i)] in 10 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 10 minutes, after which 1.12 g of (5-methyl -2-oxo-1,3-dioxolen-4-yl)methyl chloride was added, and the mixture was stirred at 60° C. for 4 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate and water. The ethyl acetate layer was separated and concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 1:15 by volume mixture of methanol and methylene chloride as the eluent, to give 1.14 g of the title compound as a viscous oil.

Aufarbeitung

  1. stirringthe mixture was stirred at 60° C. for 4 hours
  2. customThe ethyl acetate layer was separated
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customthe concentrate was purified by column chromatography through silica gel
  5. additionby volume mixture of methanol and methylene chloride as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-d2117bf2535243838646afbdf6a74d7a
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646171

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