Triethylamine → Benzyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole-1-carboxylate
Reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10].C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[N:15]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:14]=[CH:13][N:12]=1)[CH3:10]Participants
6
Procedure
To a solution of the compound of Example 58 (7.50 g, 37.4 mmol) and triethylamine (5.74 ml, 41.2 mmol) in dichloromethane (100 ml), cooled in an ice bath, was added dropwise benzyl chloroformate (21.4 ml, 150 mmol). The reaction mixture was allowed to warm to room temperature and stirred under nitrogen for 3 h. The mixture was cooled, before addition of aqueous sodium hydrogen carbonate solution and dichloromethane and the two layers were separated. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried (MgSO4) and concentrated in vacuo. To the residue was added cyclohexane and the solution was filtered and concentrated in vacuo.
Workup
- customthe two layers were separated
- extractionThe aqueous phase was extracted with dichloromethane
- dry with materialthe combined organic phases were dried (MgSO4)
- concentrationconcentrated in vacuo
- additionTo the residue was added cyclohexane
- filtrationthe solution was filtered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7cee89aaefb3424a9dfe1a570eb5966a
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547718B2
Reaction notes
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