Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | L-Norvaline | HCID 65098 | — |
| Reactant | 2-Chloro-4-fluorobenzonitrile | HCID 109000 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 67105491 | HCID 67105491 | 100% |
Reaction Steps
To a solution of 2-chloro-4-fluorobenzonitrile (5.0 g) in dimethyl sulfoxide (80 mL) were added L-norvaline (4.52 g) and cesium carbonate (13.6 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: 8.12 g, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420694B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-59e10a86eda24c819e3afae0e96ed984 |
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| Source note | uspto-grants-2013_04 |
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