Hydrochloric Acid → {5-Fluoro-2-methyl-3-[3-(pyridine-2-sulfonyl)thiophen-2-ylmethyl]indol-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:29]=[CH:28][CH:27]=[CH:26][N:25]=2)(=[O:23])=[O:22])=[C:6]1[CH3:30].[OH-].[Li+].[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:29]=[CH:28][CH:27]=[CH:26][N:25]=1)(=[O:22])=[O:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of {5-fluoro-2-methyl-3-[3-(pyridine-2-sulfonyl)thiophen-2-ylmethyl]indol-1-yl}acetic acid methyl ester (0.050 g) in tetrahydrofuran (0.30 mL) was treated with 1.0 M aqueous lithium hydroxide solution (1.0 mL), and the resulting mixture was stirred at room temperature overnight. The mixture was treated with 5.0 M aqueous sodium hydroxide solution (1.0 mL) and stirred at room temperature for 3 hours and then at 40° C. overnight. The mixture was acidified by the addition of aqueous hydrochloric acid solution and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (2:3 to 19:1 by volume) to afford the title compound as a yellow solid (0.020 g).
Workup
- stirringstirred at room temperature for 3 hours
- customat 40° C.
- customovernight
- concentrationconcentrated under reduced pressure
- customThe residue was purified by preparative reverse-phase HPLC
- washeluting with a mixture of acetonitrile and water (2:3 to 19:1 by volume)
Sources & evidence
- ORD record
- ord-23994d1ac08e4019981a9360a6374c21
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394836B2
Reaction notes
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