Ethyl Acetate → N-[3-(2-methoxycarbonylethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide

HRID 1107963Notes

Reaction equation

HRID 1107963 reaction equation
[C:1]([CH2:4][CH2:5][CH:6]1[C:14]2[C:9](=[C:10]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]([CH3:16])=[CH:12][C:13]=2[CH3:15])[NH:8][CH2:7]1)([OH:3])=[O:2].[CH3:24]COC(C)=O>CCOCC>[CH3:24][O:2][C:1]([CH2:4][CH2:5][CH:6]1[C:14]2[C:9](=[C:10]([NH:17][C:18](=[O:23])[C:19]([CH3:20])([CH3:22])[CH3:21])[C:11]([CH3:16])=[CH:12][C:13]=2[CH3:15])[NH:8][CH2:7]1)=[O:3]

Participants

4

Reactant 2

HCID 8857Ethyl Acetate2×HCID 22247340N-[3-(2-carboxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide

Product 1

HCID 22247317N-[3-(2-methoxycarbonylethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-[3-(2-Carboxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide (1.5 g) was dissolved in AcOEt (10 ml) and a solution of CH2N2 in ether was added. AcOEt (100 ml) was added, and after washing with water, the mixture was dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 1.0 g of N-[3-(2-methoxycarbonylethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide.

Workup

  1. washafter washing with water
  2. dry with materialthe mixture was dried over anhydrous sodium sulfate
  3. customAcOEt was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-76f9c208fef34a5493bb93c0fec6f3da
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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