Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Glycine tert-butyl ester | HCID 151417 | — |
| Reactant | 2-Fluoro-5-(trifluoromethyl)benzonitrile | HCID 521016 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 67307282 | HCID 67307282 | 95.8% |
Reaction Steps
To a solution of 2-fluoro-5-trifluoromethylbenzonitrile 1A (10 g, 52.9 mmol) in N-methylpyrrolidinone (NMP) (100 mL) was added glycine tert-butyl ester 5A (13.8 g, 105 mmol) and diisopropylethylamine (20 g, 155 mmol). The reaction mixture was heated at 110° C. for 4 hours. Ethyl acetate (500 mL) was added and the organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to provide (2-cyano-4-trifluoromethylphenylamino)acetic acid tert-butyl ester 5B (15.2 g, 50.7 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765757B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-5740ba24e6b5430187c4456c5c8c6eb6 |
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| Source note | uspto-grants-2014_07 |
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