Hydroxyamine hydrochloride → Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409397ノート

反応式

HRID 1409397 の反応式
[CH: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][CH3:11])=[O:9])[N:7]=1)=O.[NH2:20]O.Cl>CO>[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][CH3:11])=[O:9])[N:7]=1)#[N:20]

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 58638526methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

生成物 1

HCID 58638496Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Into a flask containing a solution of methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate (9 g, 31.6 mmol) in MeOH (200 ml), 50% aqueous NH2OH.HCl solution (2.5 ml) was added and stirred at RT for 3 h. The reaction mixture was concentrated and extracted with EtOAc. The organic layer was concentrated and the resulting residue was dissolved in DCM (200 ml). Pyridine (12 ml) and trifluoroacetic anhydride (18 ml) were added to the above mixture and stirred for 12 h. The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with DCM. The organic layer was concentrated and purified with flash chromatography. Yield 4.1 g. 1H-NMR (400 MHz; DMSO-d6): δ −0.04 (s, 9H), 0.87 (t, 2H), 3.56 (t, 2H), 3.81 (s, 3H), 5.29 (s, 2H), 8.28 (s, 1H).

後処理

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. dissolutionthe resulting residue was dissolved in DCM (200 ml)
  6. additionPyridine (12 ml) and trifluoroacetic anhydride (18 ml) were added to the above mixture
  7. stirringstirred for 12 h
  8. customThe reaction mixture was quenched with aqueous NaHCO3 solution
  9. extractionextracted with DCM
  10. concentrationThe organic layer was concentrated
  11. custompurified with flash chromatography

出典と根拠

ORDレコード
ord-6ab4675f18cb4f328b85bc5909cfb197
出典データセット
uspto-grants-2014_12
特許番号
US08921378B2

反応ノート

読み込み中…