Potassium Carbonate → 7-[[4-(2-Propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1169459Notes

Reaction equation

HRID 1169459 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:32]=[CH:31][C:11]([CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[S:23](=[O:25])(=[O:24])[CH2:22][CH2:21][C:20]([C:26]([O:28]C)=[O:27])=[CH:19][C:18]=3[CH:30]=2)=[CH:10][CH:9]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO>[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[S:23](=[O:25])(=[O:24])[CH2:22][CH2:21][C:20]([C:26]([OH:28])=[O:27])=[CH:19][C:18]=3[CH:30]=2)=[CH:31][CH:32]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22990122HCID 22990122, compound

Product 1

HCID 229901977-[[4-(2-Propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 61.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Into a solution of methyl 7-[[4-(2-propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.54 g) in THF-methanol (10-5 ml) was added at room temperature 2.4 ml of a 1 M aqueous solution of potassium carbonate (2.6 mmol), 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-[[4-(2-propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (321 mg) as light 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-70f1a457ca9547c8ae65df9892c5ddb1
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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