Hydrochloric Acid → 4-Methyl-3-[[1-oxo-2-(tricyclo[3.3.1.13,7]dec-1-yl)ethyl]amino]phenoxy-acetic acid, hydrochloride salt

HRID 1066243Notes

Reaction equation

HRID 1066243 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([NH:8][C:9](=[O:21])[CH2:10][C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33]CC)=[O:32].[OH-].[Na+].[ClH:38]>C(OCC)(=O)C.O1CCOCC1>[ClH:38].[CH3:22][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:30][C:31]([OH:33])=[O:32])=[CH:7][C:6]=1[NH:8][C:9](=[O:21])[CH2:10][C:11]12[CH2:20][CH:15]3[CH2:14][CH:13]([CH2:19][CH:17]([CH2:16]3)[CH2:18]1)[CH2:12]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 9904389N-(5-Hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

Product 1

HCID 1317225974-Methyl-3-[[1-oxo-2-(tricyclo[3.3.1.13,7]dec-1-yl)ethyl]amino]phenoxy-acetic acid, hydrochloride salt

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(5-Hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide from Example 12 (0.20 g) was added potassium carbonate (0.106 g) and ethyl bromoacetate (0.3 ml). The reaction mixture was stirred and heated at 80° C. for 24 hours. Once cooled, the reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic phase was separated, dried over magnesium sulphate (MgSO4) and evaporated under reduced pressure to leave a residue which was purified by silica gel chromatography eluting with iso-hexane/diethyl ether (1:1) to give a white solid. The solid was dissolved in dioxane (20 ml) and the solution treated with 2M sodium hydroxide solution, the reaction mixture was stirred at ambient temperature for 24 hours, acidified (2M hydrochloric acid) and extracted into ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate (MgSO4) and evaporated under reduced pressure. The residue was triturated with diethyl ether to leave the title compound as a white solid (0.070 g).

Workup

  1. temperatureOnce cooled
  2. washwashed with saturated brine
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulphate (MgSO4)
  5. customevaporated under reduced pressure
  6. customto leave a residue which
  7. customwas purified by silica gel chromatography
  8. washeluting with iso-hexane/diethyl ether (1:1)
  9. customto give a white solid
  10. stirringthe reaction mixture was stirred at ambient temperature for 24 hours
  11. extractionextracted into ethyl acetate
  12. washThe organic phase was washed with brine
  13. dry with materialdried over magnesium sulphate (MgSO4)
  14. customevaporated under reduced pressure
  15. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-a75c56731c9941ed836419f8e87b8bb5
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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