Hydrochloric Acid → HCID 22990172, compound

HRID 1169449Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Into a solution of methyl 7-[(2-methoxybenzyl)oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (230 mg) in THF-methanol (5-2.5 ml) was added at room temperature an aqueous solution (1.0 ml) of potassium carbonate (164 mg), and the resulting mixture was stirred at 60° C. for 20 hours. After cooling to room temperature, the reaction mixture was mixed with 1 N hydrochloric acid (10 ml) and 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-[(2-methoxybenzyl)oxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (172 mg) as colorless crystals.

Workup

temperatureAfter cooling to room temperature
extractionwas extracted with ethyl acetate
washThe organic layer was washed with an aqueous saturated solution of sodium chloride
dry with materialwas dried with magnesium sulfate
concentrationAfter concentration under reduced pressure
filtrationthe precipitated crystals were collected by filtration
washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record: ord-08106d916ff84ec09fba0b632da8804f
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627651B1

Reaction notes

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