Acetic Anhydride → N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]acetamide

HRID 1724060Notes

Reaction equation

HRID 1724060 reaction equation
[C:1]([NH:4][C@H:5]([C:10]([OH:12])=[O:11])[CH2:6][C:7]([OH:9])=O)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C>>[C:1]([NH:4][C@@H:5]1[C:10](=[O:11])[O:12][C:7](=[O:9])[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 65065(2S)-2-Acetamidobutanedioic acid

Product 1

HCID 11829698N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]acetamideYield 88.5%

Conditions

Temperature
80 °C

Procedure

A stirred suspension of N-Acetyl-L-aspartic acid (35.0 g, 199.9 mmol) in acetic anhydride (100 mL, 1.06 mol) was heated to 80° C. for ˜1 h until all the solid material had dissolved. The heating bath was removed, and the reaction mixture was stirred 4 h at ambient temperature. The product was collected by filtration and washed with tert-butyl methyl ether to afford N-acetyl-L-aspartic anhydride (27.8 g, 88%) as white crystals, [α]D−49.0° (c=2.5, Ac2O).

Workup

  1. dissolutionhad dissolved
  2. customThe heating bath was removed
  3. filtrationThe product was collected by filtration
  4. washwashed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-f05eff5a36bf4844b53be763f8878a2f
Source dataset
uspto-grants-2009_02
Patent number
US07485731B2

Reaction notes

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