1,2-Dibromoethane → 2-[1-Methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester

HRID 916141Notes

Reaction equation

HRID 916141 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5](=[O:28])[CH:6]([NH:15][C:16]([CH3:27])=[CH:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Br:29][CH2:30][CH2:31]Br>C(O)C>[CH3:3][O:4][C:5](=[O:28])[CH:6]([NH:15][C:16]([CH3:27])=[CH:17][C:18](=[O:26])[C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:31][CH2:30][Br:29])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 671332732-[1-Methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester

Product 1

HCID 671331222-[1-Methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl esterYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (0.17 g, 2.95 mmol) in ethanol (20 ml) is added 2-[1-methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester (1.05 g, 2.95 mmol) and 1,2-dibromoethane (5.54 g, 29.50 mmol). Then the mixture is heated to reflux for 8 hours. After cooled, the reaction mixture is filtered to remove the solid formed, and then the filtrate is evaporated under a vacuum. The crude product is purified by silica gel chromatography using hexane/EtOAc (4:1) as eluent to give the title compound (0.37 g, 27%).

Workup

  1. temperatureThen the mixture is heated
  2. temperatureto reflux for 8 hours
  3. temperatureAfter cooled
  4. filtrationthe reaction mixture is filtered
  5. customto remove the solid
  6. customformed
  7. customthe filtrate is evaporated under a vacuum
  8. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-ea5153c775ee4f319ddee8550df1dbba
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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