Hydrochloric Acid → {5-Fluoro-2-methyl-3-[2-(methylphenylsulfamoyl)benzyl]indol-1-yl}acetic acid

HRID 1944430Notes

Reaction equation

HRID 1944430 reaction equation
C[O:2][C:3](=[O:34])[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[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22](=[O:32])(=[O:31])[N:23]([CH3:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:6]1[CH3:33].[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:34])=[O:2])[C:6]([CH3:33])=[C:7]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](=[O:32])(=[O:31])[N:23]([CH3:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67044995{5-Fluoro-2-methyl-3-[2-(methylphenylsulfamoyl)benzyl]indol-1-yl}acetic acid methyl ester

Product 1

HCID 58201225{5-Fluoro-2-methyl-3-[2-(methylphenylsulfamoyl)benzyl]indol-1-yl}acetic acidYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {5-fluoro-2-methyl-3-[2-(methylphenylsulfamoyl)benzyl]indol-1-yl}acetic acid methyl ester (0.10 g) and tetrahydrofuran (0.5 mL) was treated with 2.0 M aqueous sodium hydroxide solution (2.0 mL), and the resulting mixture was stirred at room temperature for 15 hours. The mixture was acidified by the addition of 2.0 M 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 1:9 by volume) to afford the title compound as pale yellow solid (0.083 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by preparative reverse-phase HPLC
  3. washeluting with a mixture of acetonitrile and water (2:3 to 1:9 by volume)

Sources & evidence

ORD record
ord-c532a062dd27401e8552164cfa2ee908
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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