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

HRID 1531979Notes

Reaction equation

HRID 1531979 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-ea4ef6d8d7ff4ae58fe7d8df5c1290d5
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

Loading…