Ethyl Acetate → N-(3-chloro-4-cyanophenyl)-4-fluorophenylalanine

HRID 1967322Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:11][C:12]1[CH:23]=[CH:22][C:15]([CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[NH2:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([NH:18][C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][C:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:23][CH:22]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-chloro-4-fluorobenzonitrile (1.8 g) in dimethyl sulfoxide (30 mL) were added 4-fluorophenylalanine (2.54 g) and cesium carbonate (4.90 g), and the mixture was stirred at 90° C. overnight. After allowing 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: 3.69 g, 100%).

Workup

customAfter allowing 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-1c3b502b23944b5ab5ce0b2610de398a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420694B2

Reaction notes

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