Hydrochloric Acid → HCID 22927039, compound

HRID 1985419Notes

Reaction equation

HRID 1985419 reaction equation
[CH:1]([O:4][CH:5]([CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14](COC)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH3:3])[CH3:2].Cl.O.C(=O)([O-])O.[Na+]>CC(C)=O>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([CH2:11][CH:5]([O:4][CH:1]([CH3:2])[CH3:3])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 22926813HCID 22926813, compound

Product 1

HCID 22927039HCID 22927039, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.3 g of Ethyl 2-isopropoxy-3-(1-methoxymethyl-1H-indol-3-yl)propionate was dissolved in 25 ml of acetone, and 15 ml of 5N hydrochloric acid was added, and the mixture was stirred for 2 hours. The reaction solution was cooled with ice, treated with water and sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was dissolved in 20 ml of ethanol, and an aqueous solution containing 2 g of potassium carbonate was added, and the mixture was stirred at 50° C. for 3 hours. The reaction solution was cooled with ice, treated with water and ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then evaporated. The residue was subjected to silica gel column chromatography (50% ethyl acetate-hexane), to give 0.75 g of the title compound.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in 20 ml of ethanol
  7. additionan aqueous solution containing 2 g of potassium carbonate
  8. additionwas added
  9. stirringthe mixture was stirred at 50° C. for 3 hours
  10. temperatureThe reaction solution was cooled with ice
  11. additiontreated with water and ammonium chloride solution
  12. extractionextracted with ethyl acetate
  13. washThe organic layer was washed with saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customevaporated

Sources & evidence

ORD record
ord-e6ee56e0749e4f848967225f291462b7
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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