Hydrochloric Acid → HCID 22990137, compound

HRID 1169309Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Into a suspension of methyl 7-(3-pyridylmethoxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (650 mg) in THF/methanol (6/3 ml) was added at room temperature an aqueous solution (1.4 ml) of potassium carbonate (415 mg), and the resulting mixture was stirred at 60° C. for 19 hours. Into this reaction mixture was added further an aqueous solution (0.7 ml) of potassium carbonate (207 mg), and the resulting mixture was stirred further at 60° C. for 3 days. After cooling to room temperature, 1 N hydrochloric acid was added to the reaction mixture until the pH was adjusted to 7-8, and the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether to obtain methyl 7-(3-pyridylmethoxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (493 mg) as colorless crystals.

Workup

stirringthe resulting mixture was stirred further at 60° C. for 3 days
temperatureAfter cooling to room temperature
filtrationthe precipitated crystals were collected by filtration
washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record: ord-3c15d1e71c004cbca8d8758ea3150721
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627651B1

Reaction notes

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