Sodium Hydroxide → 3-[4,6-Dimethyl-7-(2,2-dimethylpropanamido)-1-octylindolin-3-yl]propionic Acid

HRID 1107965Notes

Reaction equation

HRID 1107965 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:26])[CH:14]=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]([CH2:27][CH2:28][C:29]([O:31]C)=[O:30])[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+]>CCO.O>[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:26])[CH:14]=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH:11]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15895569N-[(1-Octyl-3-(2-methoxycarbonylethyl)-4,6-dimethylindolin-7-yl)]-2,2-dimethylpropanamide

Product 1

HCID 158955703-[4,6-Dimethyl-7-(2,2-dimethylpropanamido)-1-octylindolin-3-yl]propionic AcidYield 75.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[(1-Octyl-3-(2-methoxycarbonylethyl)-4,6-dimethylindolin-7-yl)]-2,2-dimethylpropanamide (1.1 g) was dissolved in EtOH (10 ml) and a solution of NaOH (494 mg) in water (3 ml) was added, which was followed by stirring at room temperature for 30 min. EtOH was evaporated under reduced pressure and CHCl3 (50 ml) was added. After washing successively with 5% aqueous citric acid and saturated brine, the mixture was dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 800 mg of the title compound.

Workup

  1. customEtOH was evaporated under reduced pressure and CHCl3 (50 ml)
  2. additionwas added
  3. washAfter washing successively with 5% aqueous citric acid and saturated brine
  4. dry with materialthe mixture was dried over anhydrous sodium sulfate
  5. customCHCl3 was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-d898e841eed243b99768f742d70d7a07
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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