Hydrochloric Acid → HCID 69314318, compound

HRID 273414Notes

Reaction equation

HRID 273414 reaction equation
[CH2:1]([N:3]([CH2:37][CH3:38])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[C:24]([F:35])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:36])[CH:8]=1)[CH3:2].[OH-].[Na+].[ClH:41].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O1CCCC1.CO>[ClH:41].[CH2:37]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH3:36])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:24]([F:35])[CH:23]=3)[CH:15]=2)=[C:11]([CH3:13])[CH:12]=1)[CH3:38]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 58903200Ethyl 3-[4-({4'-[2-(diethylamino)ethoxy]-2',6'-dimethylbiphenyl-3-yl}methoxy)-2-fluorophenyl]propanoate

Product 1

HCID 69314318HCID 69314318, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of ethyl 3-[4-({4′-[2-(diethylamino)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methoxy)-2-fluorophenyl]propanoate (0.62 g, 1.18 mmol), methanol (5 mL) and tetrahydrofuran (10 mL) was added 1 N aqueous sodium hydroxide solution (2.4 mL) at room temperature with stirring and the mixture was stirred at the same temperature for 2 hrs. The reaction mixture was neutralized with 1 N hydrochloric acid, diluted with ethyl acetate, washed with saturated brine, dried and concentrated under reduced pressure. The residue was purified by preparative HPLC to give a colorless oil. The oil was dissolved in ethyl acetate, neutralized with saturated aqueous sodium hydrogen carbonate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and 4 N hydrogen chloride-ethyl acetate solution was added. The precipitated crystals were collected by filtration, washed and dried to give the title compound (0.20 g, yield 32%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hrs
  2. washwashed with saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC
  6. customto give a colorless oil
  7. washwashed with water and saturated brine
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. addition4 N hydrogen chloride-ethyl acetate solution was added
  12. filtrationThe precipitated crystals were collected by filtration
  13. washwashed
  14. customdried

Sources & evidence

ORD record
ord-7d4c0ade4a324162a9fd36e07b1b04f7
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

Loading…