[1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester → [1-(1-benzyl-5-methyl-1H-benzimidazol-2-yl)-2-methyl-propyl]-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:12](=O)[NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:12]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=2[N:13]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
A solution of [1-(2-benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester (400 mg, 0.97 mmol) in acetic acid (4 mL) was heated at 100° C. for 2 h. 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 (300 mg).
Workup
- customThe solvent was removed in vacuo
- dissolutionthe resulting solid was dissolved in ethyl acetate
- washThe organic layer was washed with saturated NaHCO3
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-ec89a66a38c04de7b50f7a719b19c89d
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008335B2
Reaction notes
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