Indole → 1H-Indole-5-acetic acid, 7-((2,2-dimethyl-1-oxopropyl)amino)-4,6-dimethyl-1-octyl-

HRID 1531982Notes

Reaction equation

HRID 1531982 reaction equation
N1C2C(=CC=CC=2)C=C1.[CH2:10]([N:18]1[C:26]2[C:21](=[C:22]([CH3:41])[C:23]([CH2:35][C:36]([O:38]CC)=[O:37])=[C:24]([CH3:34])[C:25]=2[NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[CH:20]=[CH:19]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[Na+]>CCO.O>[CH2:10]([N:18]1[C:26]2[C:21](=[C:22]([CH3:41])[C:23]([CH2:35][C:36]([OH:38])=[O:37])=[C:24]([CH3:34])[C:25]=2[NH:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])[CH:20]=[CH:19]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 798Indole2×HCID 14798Sodium HydroxideHCID 22247342N-(1-octyl-5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 158955711H-Indole-5-acetic acid, 7-((2,2-dimethyl-1-oxopropyl)amino)-4,6-dimethyl-1-octyl-Yield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.70·1.10 (3H, br-t, —(CH2)7CH3), 1.10- 1.70 (15H, m, —CH2 CH3, —(CH2)6CH3), 1.38 (9H, s, —C(CH3)3), 2.21 (3H, s, —CH3), 2.47 (3H, s, —CH3), 3.79 (2H, m, —CH2 CO2—), 3.90·4.30 (4H, m, —CH2 CH3, >NCH2—), 6.42 (1H, t, J=3.5 Hz, Indole C3—H), 6.91 (1H, t, J=3.5 Hz, Indole C2—H), 7.12 (1H, br, —CONH—). (3) N-(1-Octyl-5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide (3.5 g) was dissolved in EtOH (50 ml), and a solution of NaOH (1.6 g) in water (20 ml) was added, which was followed by stirring at 60° C. for 1 hr. EtOH was evaporated under reduced pressure, and the residue was dissolved in water (20 ml), and washed with AcOEt (10 ml). The aqueous layer was neutralized with 2N HCl and extracted with AcOEt (50 ml). The AcOEt layer was washed successively with saturated brine and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure to give 2.0 g of the title compound.

Workup

  1. customEtOH was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water (20 ml)
  3. washwashed with AcOEt (10 ml)
  4. extractionextracted with AcOEt (50 ml)
  5. washThe AcOEt layer was washed successively with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAcOEt was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c3ea3e115ec4409d87796ef617829894
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

Loading…