Hydrochloric Acid → [3-(2-Benzenesulfonyl-4-cyanobenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 1944415Notes

Reaction equation

HRID 1944415 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][C:19]([C:22]#[N:23])=[CH:18][C:17]=2[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[C:6]1[CH3:33].[OH-].[Li+].Cl>O1CCCC1>[C:27]1([S:24]([C:17]2[CH:18]=[C:19]([C:22]#[N:23])[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:34])=[O:2])[C:6]=2[CH3:33])(=[O:26])=[O:25])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67044517[3-(2-Benzenesulfonyl-4-cyanobenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

Product 1

HCID 58201244[3-(2-Benzenesulfonyl-4-cyanobenzyl)-5-fluoro-2-methylindol-1-yl]acetic acidYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [3-(2-benzenesulfonyl-4-cyanobenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.11 g) in tetrahydrofuran (0.30 mL) was treated with 1.0 M aqueous lithium hydroxide solution (2.0 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 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 (0.058 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-86d9a3cd8d244e8d9256cee1ef4637ee
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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