Potassium Carbonate → HCID 53746168, compound

HRID 1016617Notes

Reaction equation

HRID 1016617 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CC(C)=O>[CH3:33][O:32][C:30](=[O:31])[CH2:29][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][NH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:21])=[CH:13][C:14]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 69759657HCID 69759657, compound

Product 1

HCID 53746168HCID 53746168, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 14 (0.287 g, 1 mmol) in acetone (20 mL) was treated with K2CO3 (0.552 g, 4 mmol) and methyl bromoacetate (0.14 mL, 1.5 mmol) and refluxed for 3 h. After cooling, the reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography over silica gel using EtOAc:Hex (3:2) as eluant to give 15 as white solid (0.323 g, 90%).

Workup

  1. temperaturerefluxed for 3 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-ac166a69a9a442e08f081831046f684e
Source dataset
uspto-grants-2002_11
Patent number
US06476076B1

Reaction notes

Loading…