Potassium Carbonate → HCID 22989952, compound

HRID 1169312Notes

Reaction equation

HRID 1169312 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][C:18]([C:24]([O:26]C)=[O:25])=[CH:17][C:16]=3[CH:28]=2)=[CH:8][CH:7]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO>[CH2:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:22])(=[O:23])[CH2:20][CH2:19][C:18]([C:24]([OH:26])=[O:25])=[CH:17][C:16]=3[CH:28]=2)=[CH:29][CH:30]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22989958HCID 22989958, compound

Product 1

HCID 22989952HCID 22989952, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Into a solution of methyl 7-[[4-(propoxymethyl)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (1.15 g) in THF/methanol (10/5 ml) was added at room temperature an aqueous solution (2.1 ml) of potassium carbonate (622 mg), and the resulting mixture was stirred at 60° C. for 2 days. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate. To the aqueous layer was added 1 N hydrochloric acid until the pH was adjusted to 2-3, 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-(propoxymethyl)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (425 mg) as colorless 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 until the pH
  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-dada4a11c6984223a527ed334c6587b7
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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