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

HRID 916144Notes

Reaction equation

HRID 916144 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5](=[O:27])[CH:6]([NH:15][C:16]([CH3:26])=[CH:17][C:18](=[O:25])[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Br:28][CH2:29][CH2:30]Br>C(O)C>[CH3:3][O:4][C:5](=[O:27])[CH:6]([NH:15][C:16]([CH3:26])=[CH:17][C:18](=[O:25])[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:30][CH2:29][Br:28])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 671332772-[1-Methyl-3-oxo-3-(3-pyridyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester

Product 1

HCID 671334012-(1-Methyl-3-oxo-3-(3-pyridyl)-propenylamino)-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl esterYield 15.2%

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-(3-pyridyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester (1.00 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 (0.20 g, 15%).

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-767d533c459b49098e34e1e1facd222c
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

Loading…