Sodium Hydroxide → HCID 17858914, compound

HRID 1372698Notes

Reaction equation

HRID 1372698 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29]C)=[O:28])=[CH:22][C:21]=2[Cl:31])=[O:18])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[CH:22][C:21]=2[Cl:31])=[O:18])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17859427HCID 17859427, compound

Product 1

HCID 17858914HCID 17858914, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In THF (7.0 ml) was dissolved methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate (341.3 mg, 0.788 mmol). To the resulting solution was added 0.25N NaOH (7.0 ml). The resulting mixture was stirred at 50° C. for 18 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure. The residue was acidified with 1N HCl (2.5 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetic acid (285.8 mg, 86%) as a light pink amorphous substance.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-502146a6f5924470afa5528f3921c3c9
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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