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

HRID 1409398노트

반응식

HRID 1409398 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9a5fce4873e24aee9e8380d4d4c3cd74
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921378B2

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