Hydrochloric Acid → 7-(4-Butoxyethoxyphenyl)-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid
Reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([C:25]([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)=[O:26])[CH2:23][CH2:22][C:21]([C:32]([O:34]C)=[O:33])=[CH:20][C:19]=3[CH:36]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O.Cl>O1CCCC1.CO>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([C:25]([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)=[O:26])[CH2:23][CH2:22][C:21]([C:32]([OH:34])=[O:33])=[CH:20][C:19]=3[CH:36]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of methyl 7-(4-butoxyethoxyphenyl)-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylate (200 mg) in a mixture of tetrahydrofuran (12 ml) and methanol (12 ml) was added 1N sodium hydroxide solution (4 ml), and the mixture was stirred at room temperature for 1 day. Then, to the mixture was added water at 0° C., and 1N hydrochloric acid was further added to neutral, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, which was recrystallized from hexane-ethyl acetate to give 7-(4-butoxyethoxyphenyl)-1-(2-thienylcarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (171 mg) as yellow crystals.
Workup
- extractionwas extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried with magnesium sulfate
- customThe solvent was evaporated under reduced pressure, which
- customwas recrystallized from hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-6463e4b014af4610bb0a39e113c563f7
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06936602B1
Reaction notes
Loading…