Hydrochloric Acid → HCID 42644385, compound

HRID 1944382Notes

Reaction equation

HRID 1944382 reaction equation
C[O:2][C:3](=[O:33])[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]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:6]1[CH3:32].[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:33])=[O:2])[C:6]([CH3:32])=[C:7]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)(=[O:23])=[O:24])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67044296HCID 67044296, compound

Product 1

HCID 42644385HCID 42644385, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of {5-fluoro-3-[4-(4-fluorobenzenesulfonyl)benzyl]-2-methylindol-1-yl}acetic acid methyl ester (0.079 g) and tetrahydrofuran (1.0 mL) was treated with 5.0 M aqueous sodium hydroxide solution (1.5 mL), and the resulting mixture was stirred at 40° C. for 1 hour. The mixture was acidified by the addition of 5.0 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 (1:3 to 9:1 by volume) to afford the title compound as a white solid (0.056 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 (1:3 to 9:1 by volume)

Sources & evidence

ORD record
ord-17cf2105557a4f54b73fcecb4762cd0e
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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