Hydroxylamine → HCID 15287762, compound

HRID 1109801Notes

Reaction equation

HRID 1109801 reaction equation
[NH2:1][OH:2].[C:3]([O:12][CH2:13][CH3:14])(=[O:11])/[CH:4]=[CH:5]\[C:6]([O:8][CH2:9][CH3:10])=[O:7]>ClCCl>[OH:2][NH:1][C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][C:3]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 5271566Diethyl Maleate

Product 1

HCID 15287762HCID 15287762, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydroxylamine free base (50% aqueous solution, 45.0 g, 0.68 mol) was added dropwise to diethyl maleate (100.0 g, 0.56 mol) under nitrogen. The reaction temperature was maintained below 55° C. with an ice bath. The mixture was stirred for 30 minutes. Dichloromethane (100 ml) was added to the reaction mixture and the organic layer was collected and dried using anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to give crude diethyl N-hydroxyaspartate (103 g, 89% yield). The product was analyzed by NMR spectroscopy and found to be greater than 95% pure.

Workup

  1. temperatureThe reaction temperature was maintained below 55° C. with an ice bath
  2. customthe organic layer was collected
  3. customdried
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-87a4c1f9154742768c512da5b90d8078
Source dataset
uspto-grants-1994_06
Patent number
US05322948

Reaction notes

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