Hydrochloric Acid → [5-Fluoro-2-methyl-3-(2-phenylsulfamoylbenzyl)indol-1-yl]acetic acid

HRID 1944428Notes

Reaction equation

HRID 1944428 reaction equation
C[O:2][C:3](=[O:27])[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](Cl)(=[O:24])=[O:23])=[C:6]1[CH3:26].[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:2])=[O:27])[C:6]([CH3:26])=[C:7]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](=[O:24])(=[O:23])[NH:5][C:13]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86652191[3-(2-Chlorosulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

Product 1

HCID 67044178[5-Fluoro-2-methyl-3-(2-phenylsulfamoylbenzyl)indol-1-yl]acetic acidYield 127.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(2-chlorosulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.078 g) and tetrahydrofuran (0.5 mL) was treated with 2.0 M aqueous sodium hydroxide solution (1.0 mL), and the resulting mixture was stirred at room temperature for 20 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 19:1 by volume) to afford the title compound as a white solid (0.055 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 19:1 by volume)

Sources & evidence

ORD record
ord-476a5d5c14624eb691b93416f9aca4e8
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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