Sodium Hydroxide → HCID 17859077, compound

HRID 1372694Notes

Reaction equation

HRID 1372694 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:25][C:26]([O:28]C)=[O:27])[CH:7]=[CH:8][C:9]=1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH:22]([CH3:24])[CH3:23])[CH:14]=1)=[O:12]>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:25][C:26]([OH:28])=[O:27])[CH:7]=[CH:8][C:9]=1[NH:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH:22]([CH3:23])[CH3:24])[CH:14]=1)=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17859043HCID 17859043, compound

Product 1

HCID 17859077HCID 17859077, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In THF (6.0 ml) was dissolved the methyl 3-chloro-4-((1-isopropyl-3-indolylcarbonyl)amino)phenylacetate obtained in the above-described (Step 3). To the resulting solution was added 0.25N NaOH (6.0 ml), followed by stirring at 50° C. for 18 hours. After cooling, the reaction mixture was distilled under reduced pressure to remove the solvent. The resulting residue was acidified with 1N HCl (2.0 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give 3-chloro-4-((1-isopropyl-3-indolylcarbonyl)amino)phenylacetic acid (246.2 mg, 93%) as a brown amorphous substance.

Workup

  1. customobtained in the above-described (Step 3)
  2. temperatureAfter cooling
  3. distillationthe reaction mixture was distilled under reduced pressure
  4. customto remove the solvent
  5. customThe crystals thus precipitated
  6. filtrationwere collected by filtration under reduced pressure
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ad7c951aa88d4cba8570d2040ffc3a33
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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