Ethyl Acetate → HCID 57486677, compound

HRID 2071002Notes

Reaction equation

HRID 2071002 reaction equation
[NH2:1]/[C:2](=[N:12]\[OH:13])/[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:14][CH2:15]OC(C)=O.CC[O-].[Na+]>CCO>[CH3:14][C:15]1[O:13][N:12]=[C:2]([CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:8])[CH3:10])[N:1]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 21061511Carbamic acid, [2-(hydroxyamino)-2-iminoethyl]-, 1,1-dimethylethyl ester (9CI)

Product 1

HCID 57486677HCID 57486677, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of (Z)-tert-butyl 2-amino-2-(hydroxyimino)ethylcarbamate (945 mg, 5 mmol) and EtOAc (2.0 mL, 20.0 mmol) in EtOH (100 mL) was added a solution of NaOEt in EtOH (13 mL, 50.0 mmol) and refluxed for 6 h. The reaction mixture was cooled and all the solvent was evaporated under reduced pressure. The residue was dissolved in water and the aqueous layer was extracted with EtOAc. The combined organic layers were dried on Na2SO4 and concentrated to provide 1.0 g of tert-butyl (5-methyl-1,2,4-oxadiazol-3-yl)methylcarbamate.

Workup

  1. temperaturerefluxed for 6 h
  2. temperatureThe reaction mixture was cooled
  3. customall the solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. extractionthe aqueous layer was extracted with EtOAc
  6. customThe combined organic layers were dried on Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a6b8d848a56460690e033e369dc021c
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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