Lithium hydroxide, monohydrate → 2-Carbamoyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

HRID 1409398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409398
[C:1]([C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[C:6]([C:8]([O:10]C)=[O:9])[N:7]=1)#[N:2].[OH:20][Li].O>C1COCC1.O>[C:1]([C:3]1[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[N:7]=1)(=[O:20])[NH2:2]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58638496Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Produkt 1

HCID 709802972-Carbamoyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (3 g, 10.7 mmol) was dissolved in THF (30 ml) and H2O (8 ml). LiOH.H2O (1.1 g, 16.1 mmol) was added to the solution and the mixture was stirred at RT overnight. The reaction mixture was concentrated and acidified to pH 2 using 1 N HCl. The mixture was extracted with EtOAc and the organic layer was concentrated. Yield 2.2 g. 1H-NMR (400 MHz; DMSO-d6): δ −0.06 (s, 9H), 0.85 (t, 2H), 2.57 (s, 3H), 3.52 (t, 2H), 5.79 (s, 2H), 7.66 (s, 1H), 7.96 (s, 1H), 8.09 (s, 1H), 12.68 (s, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe mixture was extracted with EtOAc
  3. concentrationthe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9a5fce4873e24aee9e8380d4d4c3cd74
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921378B2

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