Hydrochloric Acid → [(2-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-yl)oxy]acetic acid
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH3:34])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([O:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO.Cl>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH3:34])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([O:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of methyl [(2-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-yl)oxy]acetate obtained in Example 30 (470 mg), 1 M sodium hydroxide solution (5 mL), methanol (50 mL), and tetrahydrofuran (50 mL) was stirred at room temperature for 2 h. 1 M hydrochloric acid solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (455 mg, 100%) as crystals.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-86707e154db04fa8ae9048732a7fd408
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853215B2
Reaction notes
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