Sodium Hydroxide → HCID 15287762, compound

HRID 2393765Notes

Reaction equation

HRID 2393765 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 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. concentrationconcentrated

Sources & evidence

ORD record
ord-38330a7170b447488bc560649f70e34e
Source dataset
uspto-grants-1998_09
Patent number
US05808067

Reaction notes

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