Acetic Acid → N-acetoacetyl-L-aspartic anhydride

HRID 1583900Notes

Reaction equation

HRID 1583900 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.CS(O)(=O)=O>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 6395Methanesulfonic AcidHCID 7918Acetic AnhydrideHCID 13334672N-acetoacetylaspartic acid

Product 1

HCID 13334674N-acetoacetyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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. Methanesulfonic acid, 0.20 parts by volume, was added to the slurry and the mixture was stirred for 100 minutes. The mixture initially thinned and then became thicker. Dry ethyl acetate, 20 parts by volume, was added and the resulting slurry was stirred for an additional 20 minutes. A solid was collected on a filter under a nitrogen atmosphere, rinsed with dry ethyl acetate, and then dried in a vacuum dessicator at 0.1 mm to afford 16.3 parts of N-acetoacetyl-L-aspartic anhydride, identified by the NMR spectrum in dimethylsulfoxide-D6.

Workup

  1. stirringthe resulting slurry was stirred for an additional 20 minutes
  2. customA solid was collected on
  3. filtrationa filter under a nitrogen atmosphere
  4. washrinsed with dry ethyl acetate
  5. customdried in a vacuum dessicator at 0.1 mm

Sources & evidence

ORD record
ord-6c1a35f46448420f8bc6a405b70f47b7
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

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