Lithium Hydroxide → [3-(4-Benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 1944494Notes

Reaction equation

HRID 1944494 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[S:20][N:19]=[C:18]([Cl:21])[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].[OH-].[Li+]>O1CCCC1>[C:25]1([S:22]([C:17]2[C:18]([Cl:21])=[N:19][S:20][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:23])=[O:24])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67044606[3-(4-Benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

Product 1

HCID 58201238[3-(4-Benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(4-benzenesulfonyl-3-chloroisothiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.065 g), tetrahydrofuran (20 mL) and 1.0 M aqueous lithium hydroxide solution (4.0 mL) was stirred at room temperature for 5 minutes. The mixture was concentrated under reduced pressure, acidified by the addition of 1.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 19:1 by volume) to afford the title compound as a white solid (0.050 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionacidified by the addition of 1.0 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative reverse-phase HPLC
  9. washeluting with a mixture of acetonitrile and water (1:19 to 19:1 by volume)

Sources & evidence

ORD record
ord-2e8f79801d6b44f28ebc81a7dc621ae8
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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