Potassium Carbonate → HCID 20309567, compound

HRID 972795Notes

Reaction equation

HRID 972795 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([OH:19])=[C:9]([CH:18]=1)[C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Br>CC(CC)=O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:19][CH2:26][CH:28]2[O:30][CH2:29]2)=[C:9]([CH:18]=1)[C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 20309539HCID 20309539, compound

Product 1

HCID 20309567HCID 20309567, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Methyl 3-(5-acetamido-2-hydroxybenzoyl)propionate (0.75 g, 0.0028 mole), anhydrous potassium carbonate (0.39 g, 0.0028 mole), epibromohydrin (0.78 g, 0.00565 mole) and dry ethyl methyl ketone (20 ml) were stirred and heated under reflux for 16 hours. The cooled mixture was filtered and evaporated under reduced pressure to an oil which was purified by elution from a silica column with chloroformmethanol to give methyl 3-[5-acetamido-2-(2,3-epoxypropoxy)benzoyl]propionate (0.52 g, 57%, m.p. 84°-87°).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe cooled mixture was filtered
  4. customevaporated under reduced pressure to an oil which
  5. customwas purified by elution from a silica column with chloroformmethanol

Sources & evidence

ORD record
ord-5f1724c00f9f470f82941ac178734acc
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

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