Acetic Acid → HCID 68579161, Verbindung

HRID 643500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643500
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C-]#N.[K+].[N:33]12CCN(CC1)C[CH2:34]2.CC(O)=O>O.CS(C)=O>[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:34]#[N:33])[N:23]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 9237DabcoHCID 86622894HCID 86622894, Verbindung

Produkt 1

HCID 68579161HCID 68579161, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of [3′-(2-chloro-pyrimidin-4-yloxy)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester (161 mg), potassium cyanide (76 mg) and 1,4-diazabicyclo[2,2,2]octane (13 mg) in water (0.4 ml) and DMSO (2 ml) is left at 5° C. for 4 h. This mixture is acidified with AcOH to pH 4-5, quenched with brine and extracted twice with diethyl ether. The combined organic phases are dried over sodium sulfate, the solvent is evaporated and the crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1 to afford pure [3′-(2-cyano-pyrimidin-4-yloxy)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester.

Aufarbeitung

  1. customquenched with brine
  2. extractionextracted twice with diethyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is evaporated
  5. customthe crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1

Quellen und Nachweise

ORD-Eintrag
ord-e94a73e1394a40889c7b56d585feaeb0
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700605B2

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