Acetic Acid → [1-(1-benzyl-5-methyl-1H-benzimidazol-2-yl)-2-methyl-propyl]-carbamic acid tert-butyl ester

HRID 1443624Notes

Reaction equation

HRID 1443624 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]([C:12](=O)[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[C:30](O)(=O)C>>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]([C:12]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15]2[CH:16]=[CH:17][C:18]([CH3:30])=[CH:19][C:14]=2[N:13]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 68560030[1-(2-Benzylaminophenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 66886965[1-(1-benzyl-5-methyl-1H-benzimidazol-2-yl)-2-methyl-propyl]-carbamic acid tert-butyl esterYield 90%

Procedure

A solution of [1-(2-benzylamino-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (453 mg, 1.14 mmol) in acetic acid (4 ml) was heated at 100° C. for 2 hours. The solvent was removed in vacuo and the resulting solid was dissolved in ethyl acetate. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography to give of [1-(1-benzyl-5-methyl-1H-benzimidazol-2-yl)-2-methyl-propyl]-carbamic acid tert-butyl ester (389 mg, yield 90%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resulting solid was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-07409ef411984bf895f4972db9008fea
Source dataset
uspto-grants-2010_02
Patent number
US07662581B1

Reaction notes

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