Sodium Hydroxide → HCID 17858998, compound

HRID 1372704Notes

Reaction equation

HRID 1372704 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=3)[N:20]([CH3:28])[CH:19]=2)=[O:17])=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([O:11]CC)=[O:10])[CH:7]=1.[OH-].[Na+]>C1COCC1.Cl>[Cl:1][C:2]1[C:3]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=3)[N:20]([CH3:28])[CH:19]=2)=[O:17])=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58778583Ethyl (5-chloro-2-fluoro-4-((6-fluoro-1-methyl-3-indolylcarbonyl)amino)phenyl)acetate

Product 1

HCID 17858998HCID 17858998, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (17 ml) was dissolved ethyl (5-chloro-2-fluoro-4-((6-fluoro-1-methyl-3-indolylcarbonyl)amino)phenyl)acetate (665 mg, 1.63 mmol). To the resulting solution was added 0.25N NaOH (9.81 ml, 2.45 mmol) and the mixture was stirred at room temperature for 14 hours. The reaction mixture was poured in 1N HCl (3.0 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give (5-chloro-2-fluoro-4-((6-fluoro-1-methyl-3-indolylcarbonyl)amino)phenyl)acetic acid (600 mg, 97%) as a brown solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-06cb9ecb215940f389b5ff3fa3acb3ec
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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