Potassium Carbonate → HCID 22990169, compound

HRID 1169446Notes

Reaction equation

HRID 1169446 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:32]=[CH:31][CH:30]=[CH:29][C:9]=1[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][C:18]([C:24]([O:26]C)=[O:25])=[CH:17][C:16]=2[CH:28]=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:32]=[CH:31][CH:30]=[CH:29][C:9]=1[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][C:18]([C:24]([OH:26])=[O:25])=[CH:17][C:16]=2[CH:28]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22990048HCID 22990048, compound

Product 1

HCID 22990169HCID 22990169, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Into a solution of crude methyl 7-[[2-(2-propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate 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 24 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. The resulting organic layer was concentrated under reduced pressure to obtain 7-[[2-(2-propoxyethoxy)benzyl]oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (136 mg) as a yellow amorphous substance.

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. concentrationThe resulting organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff7c9729fb5549ddacd8d5d425fc19e7
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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