Water → Methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoate

HRID 1810778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810778
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[C:4]([CH:25]=[O:26])[CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:27])=[O:14])=[C:4]([CH:25]=[O:26])[CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 114954475-((4-Bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid

Produkt 1

HCID 11575669Methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoateAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid (77.2 g) and potassium carbonate (30.5 g) in DMF (500 ml) was added dropwise a solution of iodomethane (36.5 g) in DMF (100 ml) at 0° C. under nitrogen atmosphere. After stirring for 2 hours, water was added and the mixture was extracted with ethyl acetate. After washing the organic layer with water three times and with saturated brine once, the resultant was dried with magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→hexane:ethyl acetate=4:1) to give methyl 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)-pentanoate (45.7 g) as a brown oily material.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAfter washing the organic layer with water three times
  3. dry with materialwith saturated brine once, the resultant was dried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-59f59cfae2d54007a2b37dd716cf7280
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362058B2

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