Hydrochloric Acid → 2-(5-fluoro-2-methyl-3-(2-(piperidin-1-ylsulfonyl)benzyl)-1H-indol-1-yl)acetic acid
Reaction equation
C([O:3][C:4](=[O:33])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)(=[O:25])=[O:24])=[C:7]1[CH3:32])C.[OH-].[K+].Cl>C1COCC1.O>[F:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:6]([CH2:5][C:4]([OH:33])=[O:3])[C:7]([CH3:32])=[C:8]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([N:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)(=[O:24])=[O:25]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 2-(5-fluoro-2-methyl-3-(2-(piperidin-1-ylsulfonyl)benzyl)-1H-indol-1-yl)acetic acid ethyl ester (1.23 g, 2.60 mmol) in THF (50 mL), was added a solution of potassium hydroxide (0.73 g, 13.0 mmol) in water (50 mL), and the resulting solution stirred at room temperature for 2 hours. Aqueous HCl (2N, 15 mL) was then added and the aqueous layer extracted with ethyl acetate (100 mL). The organic layers were washed with brine (2×50 mL), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The solid was triturated with diethyl ether and dried in vacuo to afford 2-(5-fluoro-2-methyl-3-(2-(piperidin-1-ylsulfonyl)benzyl)-1H-indol-1-yl)acetic acid (1.09 g, 2.45 mmol, 94%).
Workup
- extractionthe aqueous layer extracted with ethyl acetate (100 mL)
- washThe organic layers were washed with brine (2×50 mL)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customThe solid was triturated with diethyl ether
- customdried in vacuo
Sources & evidence
- ORD record
- ord-3df44295d9ee4451ad88dabb49fd463a
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168673B2
Reaction notes
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