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

HRID 1409398Notes

Reaction equation

HRID 1409398 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-9a5fce4873e24aee9e8380d4d4c3cd74
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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