Water → HCID 75488679, compound

HRID 571216Notes

Reaction equation

HRID 571216 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:15][C:16]([O:18]C)=[O:17])(=[O:4])=[O:3].O.[OH-].[Li+]>C1COCC1>[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:15][C:16]([OH:18])=[O:17])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86681628HCID 86681628, compound

Product 1

HCID 75488679HCID 75488679, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-(methylsulfonamido)-1H-indol-1-yl)acetate (620 mg, 2.196 mmol) in a 1:1 mixture of H2O and THF (10 ml), lithium hydroxide (526 mg, 21.96 mmol) was added, and the mixture was reacted for 1 hour at room temperature. The organic solvent was evaporated and 1N HCl was added to the aqueous residue (pH=2); the aqueous phase was extracted with ethyl acetate (3×20 ml), and the combined organic layers were dried over sodium sulfate. The crude was purified by flash chromatography on silica gel column (DCM:MeOH=95:5) affording 2-(4-(methylsulfonamido)-1H-indol-1-yl)acetic acid (530 mg, 1.975 mmol, 90% yield). MS/ESI+ 269.1 [MH]+.

Workup

  1. additionwas added
  2. customthe mixture was reacted for 1 hour at room temperature
  3. customThe organic solvent was evaporated
  4. addition1N HCl was added to the aqueous residue (pH=2)
  5. extractionthe aqueous phase was extracted with ethyl acetate (3×20 ml)
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. customThe crude was purified by flash chromatography on silica gel column (DCM:MeOH=95:5)

Sources & evidence

ORD record
ord-9bce6ba9e0184d0faf31fb3bde68bf10
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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