Hydrochloric Acid → Isopropyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

HRID 1698571ノート

反応式

HRID 1698571 の反応式
[CH2:1]([CH:3]([C:6]1[C:14]2[N:13]([CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[C:12](=[O:22])[N:11](C(OC(C)(C)C)=O)[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].Cl>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH:19]([O:18][C:16](=[O:17])[CH2:15][N:13]1[C:14]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[CH:9][C:10]=2[NH:11][C:12]1=[O:22])([CH3:20])[CH3:21]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 67273576tert-butyl 4-(1-ethylpropyl)-3-(2-isopropoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate

生成物 1

HCID 86632855Isopropyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate収率 85.6%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of tert-butyl 4-(1-ethylpropyl)-3-(2-isopropoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate (8.95 g, 22.1 mmol) in ethyl acetate (10 ml) was added a 4N solution of hydrogen chloride in ethyl acetate (20 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 5-20% ethyl acetate/hexane gradient mixture. The residual solid was washed with hexane to give 5.76 g (18.9 mmol, 85.6%) of the title compound as a colorless solid.

後処理

  1. extractionextracted with ethyl acetate (X2)
  2. washThe combined organic layer was washed with brine (X1)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 5-20% ethyl acetate/hexane gradient mixture
  7. washThe residual solid was washed with hexane

出典と根拠

ORDレコード
ord-a7aff7ea13304572a19bddd64bb6eab7
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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