Hydrochloric Acid → {5-Fluoro-3-[3-(pyridine-3-sulfonyl)thiophen-2-ylmethyl]-2-methylindol-1-yl}acetic acid
Reaction equation
C[O:2][C:3](=[O:31])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[S:17][CH:18]=[CH:19][C:20]=2[S:21]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)(=[O:23])=[O:22])=[C:6]1[CH3:30].[OH-].[Na+].Cl>O1CCCC1>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][C:3]([OH:31])=[O:2])[C:6]([CH3:30])=[C:7]2[CH2:15][C:16]1[S:17][CH:18]=[CH:19][C:20]=1[S:21]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)(=[O:22])=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of {5-fluoro-3-[3-(pyridine-3-sulfonyl)thiophen-2-ylmethyl]-2-methylindol-1-yl}acetic acid methyl ester (0.025 g) and tetrahydrofuran (0.8 mL) was treated with 2.0 M aqueous sodium hydroxide solution (0.5 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was acidified by the addition of 1.0 M aqueous hydrochloric acid solution, extracted with ethyl acetate and the combined organic extract was dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue triturated with diethyl ether to afford the title compound as a white solid (0.020 g).
Workup
- extractionextracted with ethyl acetate
- extractionthe combined organic extract
- dry with materialwas dried over magnesium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue triturated with diethyl ether
Sources & evidence
- ORD record
- ord-1edc2a5dcf064d23acbd922933f5cd56
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394836B2
Reaction notes
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