Acetone → N-acetoacetyl-L-aspartic anhydride

HRID 1583902Notes

Reaction equation

HRID 1583902 reaction equation
[C:1]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][C:10]([OH:12])=O)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CC(C)=O.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Mg+2].C([O-])(=O)C>C(O)(=O)C>[C:1]([NH:7][C@@H:8]1[C:13](=[O:14])[O:15][C:10](=[O:12])[CH2:9]1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7918Acetic AnhydrideHCID 8896Magnesium AcetateHCID 13334672N-acetoacetylaspartic acid2×

Product 1

HCID 13334674N-acetoacetyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-acetoacetyl-L-aspartic acid, 21.7 parts, was slurried with 20 parts by volume of dry acetone and 10.7 parts acetic anhydride. Anhydrous magnesium acetate, 0.20 parts, was dissolved in 2.0 volumes glacial acetic acid and the solution was added to the stirred slurry of N-acetoacetyl-L-aspartic acid. The mixture was stirred for 3 hours at room temperature and the solid was then collected on a filter under nitrogen. The solid was rinsed with dry ethyl acetate and then dried at 0.1 mm to afford 17.3 parts of N-acetoacetyl-L-aspartic anhydride.

Workup

  1. customthe solid was then collected on
  2. filtrationa filter under nitrogen
  3. washThe solid was rinsed with dry ethyl acetate
  4. customdried at 0.1 mm

Sources & evidence

ORD record
ord-4c079b42c97448ea922406bd989fa600
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

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