Ethyl bromoacetate → HCID 67390618, compound

HRID 910839Notes

Reaction equation

HRID 910839 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[CH:12][C:11]=2[Cl:21])[CH:3]=1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH2:19][CH3:20])(=[O:17])=[O:18])=[CH:12][C:11]=2[Cl:21])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 517045Sodium AcetateHCID 67390651HCID 67390651, compound

Product 1

HCID 67390618HCID 67390618, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product from step (iii) (0.95 g), ethyl bromoacetate (0.145 ml) and sodium acetate (0.160 g) in dry ethanol (30 ml) was heated under reflux 24 h. A further 5 equivalents of ethyl bromoacetate were added and heated for a further 48 h. The mixture was partitioned between water/ethyl acetate, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane/diethylether 1:1, yield 0.44 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux 24 h
  3. temperatureheated for a further 48 h
  4. customThe mixture was partitioned between water/ethyl acetate
  5. customthe organics separated, dried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by chromatography on silica eluting with isohexane/diethylether 1:1, yield 0.44 g

Sources & evidence

ORD record
ord-9ead2333f67d47149b9a2b8702beb9f8
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

Loading…