Sodium Hydroxide → HCID 15287762, compound

HRID 1109802Notes

Reaction equation

HRID 1109802 reaction equation
[OH-:1].[Na+].[C:3]([O:12][CH2:13][CH3:14])(=[O:11])/[CH:4]=[CH:5]\[C:6]([O:8][CH2:9][CH3:10])=[O:7].S(O)(O)(=O)=O.[NH2:20]O>>[OH:1][NH:20][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 3

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 5271566Diethyl Maleate

Product 1

HCID 15287762HCID 15287762, compoundYield 1,678%

Procedure

Sodium hydroxide (40% aqueous solution, 12.9 g, 0.129 mol) was added over 20 minutes to a stirred mixture of diethyl maleate (17.3 g, 0.1 mol) and hydroxylamine sulfate (25% aqueous, 39.0 g, 0.059 mol) during which the reaction temperature rose from 28° C. to 53° C. The reaction mixture was stirred for 30 minutes under nitrogen. The mixture was transferred to separating funnel, methylene chloride was added (50 ml), the organic layer was collected dried using anhydrous magnesium sulfate, and concentrated to give diethyl N-hydroxyaspartate (18.5 g, 0.99 mol, 90% yield).

Workup

  1. customrose from 28° C. to 53° C
  2. customto separating funnel
  3. additionmethylene chloride was added (50 ml)
  4. customthe organic layer was collected
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe8a7be3346645eb858bac2d4ba5104c
Source dataset
uspto-grants-1994_06
Patent number
US05322948

Reaction notes

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