Hydroxylamine → HCID 15287762, compound

HRID 1654266Notes

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]>>[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

Reactant 2

HCID 787Hydroxylamine

HCID 5271566Diethyl Maleate

Product 1

HCID 15287762HCID 15287762, compound

Procedure

Hydroxylamine free base (50% aqueous solution, 2.0 g, 30.3 mmol) was dropwise added to diethyl maleate (4.41 g, 25.6 mmol) and stirred for 60 minutes at 40°-45° C. to give diethyl N-hydroxyaspartate. Toluene (5.02 g) and p-toluenesulfonic acid (0.05 g, 0.26 mmol) were added to the reaction mixture and refluxed for 4.5 hours. The reaction mixture was analyzed by GLC, which showed that the reaction proceeded to give 89% diethyl 2-aminomaleate (80% yield based on the external standard).

Sources & evidence

ORD record: ord-b96b5ef852fc465399429b43f9f9b64a
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05405987

Reaction notes

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