Acetic Acid → N-acetoacetyl-L-aspartic anhydride

HRID 1583901Notes

Reaction equation

HRID 1583901 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].C(O)(=O)C.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Mg+2].C([O-])(=O)C>C(OCC)(=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 176Acetic AcidHCID 7918Acetic AnhydrideHCID 8896Magnesium AcetateHCID 13334672N-acetoacetylaspartic acid

Product 1

HCID 13334674N-acetoacetyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

N-acetoacetyl-L-aspartic acid, 21.7 parts, was mixed with 20 parts by volume of glacial acetic acid and 12.3 parts of acetic anhydride. Anhydrous magnesium acetate, 0.40 parts, was added to the slurry which thinned briefly and then thickened rapidly. After 20 minutes, the slurry was thinned by addition of 10 parts by volume of dry ethyl acetate. The resulting slurry was again thinned after an additional 15 minutes upon addition of 10 parts by volume of dry ethyl acetate. The product was collected on a filter under nitrogen after a total reaction time of 60 minutes. After the solid was rinsed with dry ethyl acetate, it was dried in a vacuum dessicator at 0.1 mm to afford 17.2 parts N-acetoacetyl-L-aspartic anhydride.

Workup

  1. customThe product was collected on
  2. filtrationa filter under nitrogen after a total reaction time of 60 minutes
  3. washAfter the solid was rinsed with dry ethyl acetate, it
  4. customwas dried in a vacuum dessicator at 0.1 mm

Sources & evidence

ORD record
ord-9040cfdbf5ff400eba2a5d5833d0ae70
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

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