Hydroxylamine → tert-butyl 2-(N'-hydroxycarbamimidoyl)acetate

HRID 2036124

Reaction equation

HRID 2036124 reaction equation
[C:1]([CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].[OH:11][NH2:12]>C(O)C.C(OCC)(=O)C>[NH2:2][C:1](=[N:12][OH:11])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 70693tert-Butyl cyanoacetate

Product 1

HCID 76589802tert-butyl 2-(N'-hydroxycarbamimidoyl)acetateYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl cyanoacetate (1.0 g) was dissolved in ethanol (10 mL), and aqueous hydroxyamine solution (50%, 0.5 mL) was added dropwise under ice-cooling. After stirring at room temperature for 5 hr, the mixture was diluted with ethyl acetate, and washed with brine, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure and ethyl acetate-hexane was added. The resulting precipitate was collected by filtration to give the object product (820 mg, 67%).

Workup

  1. temperaturecooling
  2. washwashed with brine
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure and ethyl acetate-hexane
  5. additionwas added
  6. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-5cb24c0f511844f9a84d18cd02bda7ae
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Linked notes

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