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

HRID 338090Notes

Reaction equation

HRID 338090 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-00994f3fa7044d94b2cf42d6c74d66cc
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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