p-Toluenesulfonic acid → [3-(4-Methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-carbamic acid benzyl ester

HRID 1879357ノート

反応式

HRID 1879357 の反応式
[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:12][CH2:13][CH2:14][C:15](=O)[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=1[NH2:25])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:12][CH2:13][CH2:14][C:15]1[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=2[N:25]=1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 67380324[3-(2-Amino-3-methoxy-phenylcarbamoyl)-propyl]methyl-carbamic acid benzyl ester

生成物 1

HCID 67360090[3-(4-Methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-carbamic acid benzyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

To a mixture of crude [3-(2-amino-3-methoxy-phenylcarbamoyl)-propyl]methyl-carbamic acid benzyl ester acid in 7 mL toluene were added a few drops of DMF and 523 mg of TsOH and the reaction mixture was heated at 150° C. for 2.5 h in the microwave. Sat. aq. NaHCO3 solution was added, the phases were separated and the organic phase was washed with brine. The combined organic phases were dried over MgSO4, and concentrated in vacuo. Purification by CC EtOAc/MeOH (10:1) yielded 0.74 g of the desired compound as brown foam.

後処理

  1. customthe phases were separated
  2. washthe organic phase was washed with brine
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by CC EtOAc/MeOH (10:1)

出典と根拠

ORDレコード
ord-11d60e0e76f24498ab0e327f25c9b9ab
出典データセット
uspto-grants-2012_11
特許番号
US08314253B2

反応ノート

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