Hydroxyamine hydrochloride → tert-Butyl N-allyl-N-[2-hydroxyimino-2-phenyl-ethyl]carbamate

HRID 1618993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618993
[CH2:1]([N:4]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([N:4]([CH2:12][C:13](=[N:22][OH:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]

Komponenten

6

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86697893tert-Butyl N-allyl-N-phenacyl-carbamate

Produkt 1

HCID 86697903tert-Butyl N-allyl-N-[2-hydroxyimino-2-phenyl-ethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of tert-butyl N-allyl-N-phenacyl-carbamate (3.2 g, 11.6 mmol), hydroxylamine hydrochloride (1.2 g, 17.4 mmol) and sodium acetate (1.4 g, 17.4 mmol) in ethanol (46 mL) is stirred at 70° C. for 18 hours. The reaction is cooled, diluted with water and extracted with dichloromethane. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound as a mixture of E and Z isomers which is used without further purification (3.16 g, 94%). ES/MS (m/e): 191 (M+H-100).

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-39fce4feccf94ce8adc6bc0c545719bb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772282B2

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