4-formyl-N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]benzamide → 4-Formyl-N,N-bis(1H-imidazol-2-ylmethyl)benzamide
Reaction equation
[CH:1]([C:3]1[CH:39]=[CH:38][C:6]([C:7]([N:9]([CH2:24][C:25]2[N:26](COCC[Si](C)(C)C)[CH:27]=[CH:28][N:29]=2)[CH2:10][C:11]2[N:12](COCC[Si](C)(C)C)[CH:13]=[CH:14][N:15]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2]>FC(F)(F)C(O)=O.ClCCl>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]([CH2:24][C:25]2[NH:26][CH:27]=[CH:28][N:29]=2)[CH2:10][C:11]2[NH:15][CH:14]=[CH:13][N:12]=2)=[O:8])=[CH:38][CH:39]=1)=[O:2]Participants
3
Procedure
To the compound 40 (1.7 g), a 50% trifluoroacetic acid-dichloromethane solution (10 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and an aqueous 5N sodium hydroxide solution (15 mL) was added to the residue. The aqueous layer was extracted three times with 50 mL of dichloromethane. The combined organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was concentrated to obtain the title compound (compound B) (922 mg) having the following physical properties.
Workup
- concentrationThe reaction mixture was concentrated
- additionan aqueous 5N sodium hydroxide solution (15 mL) was added to the residue
- extractionThe aqueous layer was extracted three times with 50 mL of dichloromethane
- washThe combined organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe solvent was concentrated
Sources & evidence
- ORD record
- ord-a30393c4b638466c88b7e494e395eefb
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822459B2
Reaction notes
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