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

HRID 1409398ノート

反応式

HRID 1409398 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-9a5fce4873e24aee9e8380d4d4c3cd74
出典データセット
uspto-grants-2014_12
特許番号
US08921378B2

反応ノート

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