Trifluoroacetic acid → HCID 67213375, compound
Reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH:8]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH:7]2[N:20]([C:23](=[O:39])[CH:24]([NH:31]C(OC(C)(C)C)=O)[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:21][CH2:22][CH:6]12)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH:8]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH:7]2[N:20]([C:23](=[O:39])[CH:24]([NH2:31])[CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[CH2:21][CH2:22][CH:6]12)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution containing 50 (226 mg, 0.42 mmol) in DCM (5 mL) was cooled to 0° C. TFA (2 mL) was added and the reaction mixture was warmed to ambient temperature. After 90 min, the reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc and the resultant organic solution was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 172 mg of 51 as an off-white-colored foam which was used without further purification. Mass spectrum, m/z [443.3] (M+H)+.
Workup
- temperaturethe reaction mixture was warmed to ambient temperature
- concentrationthe reaction mixture was concentrated in vacuo
- dissolutionThe residue was dissolved in EtOAc
- washthe resultant organic solution was washed successively with saturated aqueous NaHCO3 and brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-646ce657b9024534bca6cbfbd416f4a9
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399683B2
Reaction notes
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