Hydrochloric Acid → [3-(2-Benzenesulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 1944472Notes

Reaction equation

HRID 1944472 reaction equation
C[O:2][C:3](=[O:32])[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]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[C:6]1[CH3:31].O1CCCC1.[OH-].[Na+].Cl>CO>[C:25]1([S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=3)[N:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]=2[CH3:31])(=[O:24])=[O:23])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67044183HCID 67044183, compound

Product 1

HCID 23725171[3-(2-Benzenesulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acidYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [3-(2-benzenesulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.17 g), tetrahydrofuran (3.0 mL) and methanol (1.5 mL) was treated with 1.0 M aqueous sodium hydroxide solution (1.5 mL), and the resulting mixture was stirred at room temperature for 2 hours. The mixture was acidified by the addition of 1.0 M aqueous hydrochloric acid solution (1.5 mL) and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as a cream solid (0.13 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-820b70b300a74f3a83c7b89b2342045c
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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