Hydroxylamine → HCID 15287762, compound

HRID 2393764Notes

Reaction equation

HRID 2393764 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. 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. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-637ebe4fe34f44d8bcfac0ace7da2aa4
Source dataset
uspto-grants-1998_09
Patent number
US05808067

Reaction notes

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