Water → Ethyl N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylphenyl}glycinate

HRID 1007495Notes

Reaction equation

HRID 1007495 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17]([NH2:21])=[CH:16][C:15]=3[CH3:22])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C([O-])(=O)C.[Na+].O>C(O)C>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:15]([CH3:22])=[CH:16][C:17]([NH:21][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][C:19]=3[CH3:20])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 517045Sodium AcetateHCID 226697004-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylaniline

Product 1

HCID 22669446Ethyl N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylphenyl}glycinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

210 mg of 4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylaniline (Example XV) are brought under reflux with 119 mg of ethyl bromoacetate and 117 mg of sodium acetate in 10 ml of ethanol for 24 h. After addition of water, the mixture is extracted with ether, and the organic phase is dried and concentrated in a rotary evaporator. By chromatographic purification (cyclohexane/ethyl acetate), 143 mg (53%) of ethyl N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylphenyl} glycinate are obtained.

Workup

  1. extractionthe mixture is extracted with ether
  2. customthe organic phase is dried
  3. concentrationconcentrated in a rotary evaporator
  4. customBy chromatographic purification (cyclohexane/ethyl acetate), 143 mg (53%) of ethyl N-{4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylphenyl} glycinate
  5. customare obtained

Sources & evidence

ORD record
ord-8cb5f2a0cd964e3eabd9bd27f4153850
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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