Potassium Carbonate → 4-[2-(3-Chloro-4-methoxycarbonyl-phenoxy)-acetyl]-piperazine-1-carboxylic Acid Tert-butyl Ester

HRID 220854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220854
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[Cl:11].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:29])[CH2:27]Br)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH2:22][N:23]([C:26](=[O:29])[CH2:27][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:12])=[C:5]([Cl:11])[CH:6]=2)[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl esterHCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

Produkt 1

HCID 575553524-[2-(3-Chloro-4-methoxycarbonyl-phenoxy)-acetyl]-piperazine-1-carboxylic Acid Tert-butyl EsterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Chloro-4-hydroxy-benzoic acid methyl ester from example E41b (2.0 g, 10.9 mmol) and 4-(2-Bromo-acetyl)-piperazine-1-carboxylic acid tert-butyl ester from Example E41a (3.68 g, 12.0 mmol) in acetonitrile (30 ml) were treated with potassium carbonate (1.6 g, 11.5 mmol), and the mixture heated at reflux 18 h. before the solvents were removed in vacuo. The residue was adsorbed onto silica gel and purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% cyclohexane to 50% EtOAc:50% cyclohexane to 70% EtOAc:30% cyclohexane) to yield the title compound (4.5 g, 100%).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux 18 h. before the solvents
  3. customwere removed in vacuo
  4. custompurified by flash chromatography on silica gel (eluant; 20% EtOAc:80% cyclohexane to 50% EtOAc:50% cyclohexane to 70% EtOAc:30% cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-1f5b83af3f014c1daa9f0899622a978e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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