反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[NH2:11])=[O:5])[CH3:2].[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH:21]=O.[BH3-]C#N.[Na+].CC(O)=O>CO>[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][NH:11][C:10]1[CH:9]=[CH:8][NH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]参加物
6
実験手順
A reaction mixture of 3-amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.77 g, 4.99 mmol), 1H-benzoimidazole-2-carboxaldehyde (0.88 g, 5.99 mmol), NaCNBH3 (0.31 g, 4.99 mmol) and HOAc (0.57 mL, 9.99 mmol) in methanol (15 mL) was stirred at r.t. overnight. The mixture was then heated at 50° C. for 5 h. Cooled to r.t. and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate (1:0 to 0:1), obtaining 1.15 g (81%) of the title compound.
後処理
- temperatureThe mixture was then heated at 50° C. for 5 h
- temperatureCooled to r.t.
- customevaporated in vacuo
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with water
- extractionThe aqueous phase was extracted with ethyl acetate (twice)
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated
- customThe crude product was purified by flash column chromatography (heptane/ethyl acetate (1:0 to 0:1)
出典と根拠
- ORDレコード
- ord-6b5f3f91fcb74e599bb6787659d0c083
- 出典データセット
- uspto-grants-2014_10
- 特許番号
- US08859568B2
関連ノート
読み込み中…