Potassium Carbonate → HCID 22990007, compound

HRID 1169465Notes

Reaction equation

HRID 1169465 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH3:35])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[S:18](=[O:20])(=[O:19])[CH2:17][CH2:16][C:15]([C:21]([O:23]C)=[O:22])=[CH:14][C:13]=2[CH:25]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH3:35])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[S:18](=[O:20])(=[O:19])[CH2:17][CH2:16][C:15]([C:21]([OH:23])=[O:22])=[CH:14][C:13]=2[CH:25]=1)[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 70024383HCID 70024383, compound

Product 1

HCID 22990007HCID 22990007, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Into a solution of methyl 7-[[3-ethoxy-4-(propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.76 g) in THF-methanol (10-5 ml) was added at room temperature a 1 M aqueous solution of potassium carbonate (3.0 ml), and the resulting mixture was stirred at 65° C. for 20 hours. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate. To the aqueous layer was added 1 N hydrochloric acid (10 ml), and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether to obtain 7-[[3-ethoxy-4-(2-propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (178 mg) as yellow crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. additionTo the aqueous layer was added 1 N hydrochloric acid (10 ml)
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialwas dried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. filtrationthe precipitated crystals were collected by filtration
  9. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-b86e2d1a67e14c5780ee709d1d9b6a67
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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