Diisopropylethylamine → N-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-3,3,3-trifluoro-propionamide
Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:23]([SiH2:27][O:28][C:29]([CH3:40])([CH3:39])[C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:33][NH2:34])([CH3:26])([CH3:25])[CH3:24].CCN(C(C)C)C(C)C.[F:50][C:51]([F:57])([F:56])[CH2:52][C:53](O)=[O:54]>C(Cl)Cl>[C:23]([SiH2:27][O:28][C:29]([CH3:40])([CH3:39])[C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:33][NH:34][C:53](=[O:54])[CH2:52][C:51]([F:57])([F:56])[F:50])([CH3:26])([CH3:24])[CH3:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
TBTU (3.37 g, 10.5 mmol) was added to a sol. of 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine (2.00 g, 7.00 mmol), DIPEA (4.80 mL, 28.0 mmol) and 3,3,3-trifluoropropionic acid (0.927 mL, 10.5 mmol) in CH2Cl2 (70 mL). The mixture was stirred at rt for 1 h. CH2Cl2 (30 mL) was added, and the mixture was washed with aq. sat. NH4Cl (2×), aq. 1M NaOH (1×) and brine (1×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 40:60) yielded the title compound (1.80 g, 65%). LC-MS: tR=1.10 min; ES+: 396.15.
Workup
- washthe mixture was washed with aq. sat. NH4Cl (2×), aq. 1M NaOH (1×) and brine (1×)
- dry with materiallayer was dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the crude by FC (EtOAc/heptane 40:60)
Sources & evidence
- ORD record
- ord-6aa8a4533d524adea870bf9fe9426107
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799805B2
Reaction notes
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