Water → Methyl 4-{[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

HRID 8133

Reaktionsgleichung

Reaktionsgleichung von HRID 8133
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]2[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=2[CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.Br[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)(O)[O-].[Na+].O>C(#N)C>[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]2[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=2[CH2:10][CH2:11][N:12]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 84580Ethyl 5-bromovalerateHCID 516892Sodium BicarbonateHCID 22014995Methyl 4-({2-[2-(4-bromobenzyloxy)phenyl]ethylamino}methyl)benzoate

Produkt 1

HCID 22015004Methyl 4-{[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5.00 g (11.0 mmol) of methyl 4-[({2-[(4-bromobenzyl)oxy]phenethyl}amino)-methyl]benzoate from Ex. VIII, 2.30 g (11.0 mmol) of ethyl 5-bromovalerate and 1.109 g (13.21 mmol) of sodium bicarbonate in 30 ml of acetonitrile are heated at reflux for 18 hours. The reaction mixture is admixed with water and extracted with methylene chloride. The organic phase is washed with saturated sodium chloride solution and dried over magnesium sulphate and the solvent is distilled off under reduced pressure. The residue is purified by chromatography over silica gel using the mobile phase methylene chloride/methanol 100/1.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. extractionextracted with methylene chloride
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by chromatography over silica gel using the mobile phase methylene chloride/methanol 100/1

Quellen und Nachweise

ORD-Eintrag
ord-e2e6007ce93047669f9a428003aa1d63
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087644B1

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