Potassium Carbonate → Methyl 2-{[2-(3,5-difluorophenyl)-2-oxoethyl]amino}-2-methylpropanoate

HRID 1864844

Reaction equation

HRID 1864844 reaction equation
Cl.[NH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[F:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:14](=[O:17])[CH2:15]Br.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[F:10][C:11]1[CH:12]=[C:13]([C:14](=[O:17])[CH2:15][NH:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5])[CH:18]=[C:19]([F:21])[CH:20]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27783312-Bromo-1-(3,5-difluorophenyl)ethanoneHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 66955347Methyl 2-{[2-(3,5-difluorophenyl)-2-oxoethyl]amino}-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl α-aminoisobutyrate hydrochloride (10.3 g, 67.0 mmol), 3,5-difluorophenacyl bromide (15.0 g, 63.8 mmol), and K2CO3 (17.6 g, 128 mmol) in DMF (100 mL) was stirred at ambient temperature for 3 h. Saturated aqueous NaHCO3 (400 mL) was added and the mixture was extracted with EtOAc (1 L). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 0:100, to give the title compound. MS: m/z=272 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (1 L)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-6ae01c68c7dd48189e1abc5e5e2c84a7
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Linked notes

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