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

HRID 1879357노트

반응식

HRID 1879357 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 1140Toluene용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-11d60e0e76f24498ab0e327f25c9b9ab
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314253B2

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