Sodium Carbonate → HCID 22329264, compound

HRID 586921Notes

Reaction equation

HRID 586921 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:11]1([NH:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+]>O.CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]([CH:11]2[CH2:12][CH2:13]2)[CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[C:6]([CH:7]=[O:8])[CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 22329113HCID 22329113, compound

Product 1

HCID 22329264HCID 22329264, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

5-bromo-2-fluorobenzaldehyde (20 g), t-butyl N-cyclopropyl-4-aminobutyrate (14.5 g), sodium carbonate (13.8 g), water (70 ml) and DMSO (70 ml) were heated at 80° C. for 5 days and at 110° C. for 3 days, which was poured into water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give t-butyl N-(4-bromo-2-formylphenyl)-N-cyclopropyl-4-aminobutyrate (6.4 g) as red oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1d5f0cd5380548f48d4804c87c587819
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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