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

HRID 1879357Notes

Reaction equation

HRID 1879357 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-11d60e0e76f24498ab0e327f25c9b9ab
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

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