Hydrochloric Acid → HCID 57905944, compound

HRID 1670077Notes

Reaction equation

HRID 1670077 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](=[O:11])([O-])[O-:9].[K+].[K+].C(OC(=O)CCC[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br)[C:23]=1CCC(OCC)=O)C.[OH-].[Na+].Cl.C[N:47]([CH:49]=[O:50])C>CC(C)=O>[O:9]1[C:31]2[CH:32]=[CH:33][C:28]([C:24]3[CH:25]=[C:26]([CH:27]=[C:22]([OH:21])[CH:23]=3)[C:49]([NH:47][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:50])=[CH:29][C:30]=2[O:11][CH2:8]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 996PhenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 57905944HCID 57905944, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of a phenol (0.3 mmol) in a mixture of acetone and DMF (2:1, 2 mL) were added potassium carbonate (10 eq.) and 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.1 eq). The resulting mixture was stirred at 75° C. for 2 days. Then the insoluble material was filtered out and the filtrate was diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and used for the next step without further purification. The total amount of material from the previous step was dissolved in EtOH (2 mL), followed by addition of 10 M NaOH solution (10 eq.). The resulting reaction mixture was stirred at room temperature overnight. Then it was neutralized with 3 N HCl and extracted into ethyl acetate. The organic extract was washed with water and brine and dried over anhydrous sodium sulfate. The crude material was purified by reverse-phase HPLC.

Workup

  1. filtrationThen the insoluble material was filtered out
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customused for the next step without further purification
  8. dissolutionThe total amount of material from the previous step was dissolved in EtOH (2 mL)
  9. customThe resulting reaction mixture
  10. stirringwas stirred at room temperature overnight
  11. extractionextracted into ethyl acetate
  12. extractionThe organic extract
  13. washwas washed with water and brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe crude material was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-1071ae183398493380570ea4630418a1
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

Loading…