tert-Butanol → HCID 67360378、化合物

HRID 1747475ノート

反応式

HRID 1747475 の反応式
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH:18]=[CH:19][NH:20]3)[C:7]1=[O:26].C([OH:32])(C)(C)C>[Zn]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]3[C:17]=2[CH2:18][C:19](=[O:32])[NH:20]3)[C:7]1=[O:26]

参加物

4

反応物 2

HCID 6386tert-ButanolHCID 67361638HCID 67361638、化合物

生成物 1

HCID 67360378HCID 67360378、化合物収率 36%

試薬・触媒・溶媒 1

HCID 23994Zinc触媒

実験手順

3-[3-(6-Chloro-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-propionic acid methyl ester (248 mg, 0.64 mmol) is dissolved it tert-butanol (20 mL) at 40° C. The reaction is stirred and pyridiniumtrbromide is added portion wise over 5 minutes. The reaction is stirred for 10 minutes and concentrated in vacuo. The crude material is dissolved in acetic acid (10 mL) and zinc powder (211 mg, 3.2 mmol)is added to the reaction. The reaction is stirred at room temperature for one hour, then the solvent evaporated in vacuo. The residue is taken up in dimethyl sulfoxide and filtered. The crude material is purified by preparative reverse phase LC to give the title compound (34 mg 0.09 mmol, 36%).

後処理

  1. additionpyridiniumtrbromide is added portion wise over 5 minutes
  2. stirringThe reaction is stirred for 10 minutes
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material is dissolved in acetic acid (10 mL)
  5. stirringThe reaction is stirred at room temperature for one hour
  6. customthe solvent evaporated in vacuo
  7. filtrationfiltered
  8. customThe crude material is purified by preparative reverse phase LC

出典と根拠

ORDレコード
ord-2874c84eeabf4447a908dee6f6c191d3
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

反応ノート

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