N-[4-(diethoxymethyl)benzyl]-N-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]-1H-imidazole-2-carboxamide → N-(4-formylbenzyl)-N-(1H-imidazol-2-ylmethyl)-1H-imidazole-2-carboxamide
Reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:33]=[CH:32][C:8]([CH2:9][N:10]([CH2:18][C:19]2[N:20](COCC[Si](C)(C)C)[CH:21]=[CH:22][N:23]=2)[C:11]([C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)=[O:12])=[CH:7][CH:6]=1)C>FC(F)(F)C(O)=O.ClCCl>[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:18][C:19]2[NH:20][CH:21]=[CH:22][N:23]=2)[C:11]([C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)=[O:12])=[CH:32][CH:33]=1)=[O:3]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To the compound 17 (970 mg), a 50% trifluoroacetic acid-dichloromethane solution (10 mL) was added under ice cooling. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and an aqueous 2N sodium hydroxide solution (20 mL) was added to the residue. The aqueous layer was extracted twice with dichloromethane (50 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated to obtain the title compound having the following physical properties. The obtained compound was used in the following reaction without being purified.
Workup
- concentrationThe reaction mixture was concentrated
- additionan aqueous 2N sodium hydroxide solution (20 mL) was added to the residue
- extractionThe aqueous layer was extracted twice with dichloromethane (50 mL)
- washThe combined organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-46777eff6d484156ae59531c7f0e2f50
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822459B2
Reaction notes
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