Hydrochloric Acid → HCID 10310671, compound

HRID 1766694Notes

Reaction equation

HRID 1766694 reaction equation
C[O:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][C:8]2[C:9]([CH3:26])=[CH:10][C:11]([NH:17][C:18](=[O:25])[CH2:19][C:20]([O:22]CC)=[O:21])=[C:12]3[C:16]=2[CH2:15][CH2:14][CH2:13]3)=[CH:5][C:4]=1[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37]C)=[CH:33][CH:32]=1.B(Br)(Br)Br.CO.Cl>ClCCl>[OH:2][C:3]1[CH:28]=[CH:27][C:6]([O:7][C:8]2[C:9]([CH3:26])=[CH:10][C:11]([NH:17][C:18](=[O:25])[CH2:19][C:20]([OH:22])=[O:21])=[C:12]3[C:16]=2[CH2:15][CH2:14][CH2:13]3)=[CH:5][C:4]=1[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25134Boron tribromideHCID 23031105HCID 23031105, compound

Product 1

HCID 10310671HCID 10310671, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl N-(7-{4-methoxy-3-[2-(4-methoxyphenyl)ethyl]phenoxy}-6-methylindan-4-yl)malonamate (40 mg) was dissolved in dichloromethane (5 mL). Adding dropwise a 1 mol/L solution of boron tribromide in dichloromethane (1 mL) under dry ice/acetone-cooling, the solution was stirred at room temperature for 24 hours. To the reaction mixture was added dropwise methanol (5 mL) under ice-cooling with stirring. Adding diluted hydrochloric acid, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. To the residue were added methanol (5 mL) and a 1 mol/L aqueous solution of sodium hydroxide (5 mL), and the mixture was stirred under an argon atmosphere at 50° C. for 30 min. The reaction mixture was evaporated under reduced pressure to dryness and water (10 mL) was added thereto. The mixture was washed with diethyl ether (10 mL) twice. To the aqueous layer were added 1 mol/L hydrochloric acid (20 mL) and brine (10 mL), and the aqueous layer was extracted with ethyl acetate (10 mL) twice. The organic layer was dried over anhydrous magnesium sulfate and evaporated-under reduced pressure to dryness to give the title compound (20 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringwith stirring
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. additionTo the residue were added methanol (5 mL)
  9. stirringa 1 mol/L aqueous solution of sodium hydroxide (5 mL), and the mixture was stirred under an argon atmosphere at 50° C. for 30 min
  10. customThe reaction mixture was evaporated under reduced pressure to dryness and water (10 mL)
  11. additionwas added
  12. washThe mixture was washed with diethyl ether (10 mL) twice
  13. additionTo the aqueous layer were added 1 mol/L hydrochloric acid (20 mL) and brine (10 mL)
  14. extractionthe aqueous layer was extracted with ethyl acetate (10 mL) twice
  15. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and evaporated-under reduced pressure to dryness

Sources & evidence

ORD record
ord-46ef0fd3731144fabfb0aed949ce1d11
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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