Potassium Carbonate → t-But yl 4-(4-bromo-2-formylphenyl)propylaminobutyrate

HRID 586879Notes

Reaction equation

HRID 586879 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH3:3].[Br:15][C:16]1[CH:17]=[CH:18][C:19](F)=[C:20]([CH:23]=1)[CH:21]=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:3][CH2:2][CH2:1][NH:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])=[C:20]([CH:21]=[O:22])[CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 22329227t-Butyl 4-propylaminobutyrate

Product 1

HCID 86759831t-But yl 4-(4-bromo-2-formylphenyl)propylaminobutyrateYield 52.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of t-butyl 4-propylaminobutyrate (14.2 g, 70.7 mmol) in DMF (20 ml) were added 5-bromo-2-fluorobenzaldehyde (14.4 g, 70.9 mmol) and potassium carbonate (14.7 g, 106 mmol) at room temperature, and the mixture was stirred at 80° C. for 94 hours. The mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1) to give yellow oil of t-but yl 4-(4-bromo-2-formylphenyl)propylaminobutyrate (14.2 g, 52%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9ac442a0ed8046058bfddb7989bf2ef6
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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