Water → HCID 90281978, compound

HRID 1497511Notes

Reaction equation

HRID 1497511 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].O>CN(C)C=O>[C:28]([O:27][C:25](=[O:26])[CH2:24][NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:8])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 59478867HCID 59478867, compound

Product 1

HCID 90281978HCID 90281978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-(2-aminoethyl)benzoate (900 mg) in N,N-dimethylformamide (20.0 mL) were added potassium carbonate (600 mg) and tert-butyl bromoacetate (0.600 mL) under ice-cooling, followed by stirring at room temperature for 5 hours. To the reaction suspension was added water, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 3-{2-[(2-tert-butoxy-2-oxoethyl)amino]ethyl}benzoate (738 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0a6e9f0123314754b91942d091e05920
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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