Ethyl Acetate → HCID 67307282, compound

HRID 1615600Notes

Reaction equation

HRID 1615600 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[C:14]([O:18][C:19](=[O:22])[CH2:20][NH2:21])([CH3:17])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN1CCCC1=O>[C:14]([O:18][C:19](=[O:22])[CH2:20][NH:21][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrile

Product 1

HCID 67307282HCID 67307282, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

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).

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe organic solvent was evaporated under reduced pressure
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-5740ba24e6b5430187c4456c5c8c6eb6
Source dataset
uspto-grants-2014_07
Patent number
US08765757B2

Reaction notes

Loading…