Ethyl Acetate → HCID 67105481, compound
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])=[CH:15][CH:14]=1)#[N:12].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([NH:19][C@H:18]([C:20]([OH:22])=[O:21])[CH2:17][C:16]2[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:24][CH:23]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 2-chloro-4-fluorobenzonitrile (0.90 g) in dimethyl sulfoxide (20 mL) were added 4-cyanophenylalanine (1.00 g) and cesium carbonate (2.23 g), and the mixture was stirred at 90° C. overnight. After warming to room temperature, ethyl acetate was added, and the mixture was extracted twice with saturated aqueous sodium hydrogen carbonate solution. The aqueous layers were combined, and acidified with citric acid, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound as a brown oil (yield: 1.57 g, 92%).
Workup
- temperatureAfter warming to room temperature
- extractionthe mixture was extracted twice with saturated aqueous sodium hydrogen carbonate solution
- extractionthe mixture was extracted twice with ethyl acetate
- washwashed with saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-60a1b3593c1c4647b7f44573d16d1463
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420694B2
Reaction notes
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