O-Methylhydroxylamine → 2-[1-(Methoxyimino)propyl]-5-(4-methanesulfonamidophenyl)-3-hydroxy-2-cyclohexen-1-one

HRID 2164361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2164361
O1CCCC1.[OH:6][C:7]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)[CH2:10][C:9](=[O:24])[C:8]=1[C:25](=O)[CH2:26][CH3:27].[CH3:29][O:30][NH2:31].C[O-].[Na+]>CO>[CH3:29][O:30][N:31]=[C:25]([C:8]1[C:9](=[O:24])[CH2:10][CH:11]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:17][CH:18]=2)[CH2:12][C:7]=1[OH:6])[CH2:26][CH3:27]

Komponenten

6

Edukt 4

HCID 4113O-MethylhydroxylamineHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 178458872HCID 178458872, Verbindung

Produkt 1

HCID 1360263062-[1-(Methoxyimino)propyl]-5-(4-methanesulfonamidophenyl)-3-hydroxy-2-cyclohexen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Into 10 ml of tetrahydrofuran was dissolved 1.2 g of 3-hydroxy-5-(4-methanesulfonamidophenyl)-2-propionyl-2-cyclohexen-1-one and to the solution were added 0.6 g of methoxyamine hydrocholorate salt and 1.4 g of methanol containing 28% of sodium methylate. Then, the mixture was kept for 15 hours at room temperature and an insoluble material was filtered off from it and the resulting filtrate solution was concentrated under reduced pressure. Its residue was dissolved in chloroform and the solution was washed with a dilute hydrochloric acid solution and water, and it was dried with anhydrous magnesium sulfate. The chloroform was distilled off from it under a reduced pressure and ethyl ether was add in it. Thus, the crystal sedimented is collected with a filtering step and 1.2 g of the desired compound as colorless crystals having a melting point of 150°-151° C. was obtained.

Aufarbeitung

  1. filtrationan insoluble material was filtered off from it
  2. concentrationthe resulting filtrate solution was concentrated under reduced pressure
  3. dissolutionIts residue was dissolved in chloroform
  4. washthe solution was washed with a dilute hydrochloric acid solution and water, and it
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. distillationThe chloroform was distilled off from it under a reduced pressure and ethyl ether
  7. additionwas add in it
  8. customThus, the crystal sedimented is collected with a filtering step and 1.2 g of the desired compound as colorless crystals
  9. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-0599ebf1d71649a498e6c175521a8be7
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04504305

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