Hydrochloric Acid → 7-(3,4-Diethoxybenzyloxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1169506Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[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+].Cl>C1COCC1.CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[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

Conditions

Temperature: 60 °C

Procedure

To methyl 7-(3,4-diethoxybenzyloxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (818 mg) dissolved in THF-methanol (15-7.5 ml) was added a 2 M aqueous solution of potassium carbonate (1.5 ml), and the resulting mixture was stirred at 60° C. for 14 hours. The reaction mixture was treated with 1 N hydrochloric acid to bring the pH to 2. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with anhydrous magnesium sulfate. After evaporation under reduced pressure to remove the solvent, the precipitated crystals were washed with hexane-ethyl acetate to obtain 7-(3,4-diethoxybenzyloxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (3.02 g) as white crystals.

Workup

extractionThe resulting mixture was extracted with ethyl acetate
washthe organic layer was washed with an aqueous saturated solution of sodium chloride
dry with materialwas dried with anhydrous magnesium sulfate
customAfter evaporation under reduced pressure
customto remove the solvent
washthe precipitated crystals were washed with hexane-ethyl acetate

Sources & evidence

ORD record: ord-4fb219c52926491bac0be73c2a3f7fe6
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627651B1

Reaction notes

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