Acetic Anhydride → N-acetoacetyl-L-aspartic anhydride

HRID 325275Notes

Reaction equation

HRID 325275 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(OC(=O)C)(=O)C.C([O-])(=O)C.[Mg+2].C([O-])(=O)C.C(OCC)(=O)C>CO>[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 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 8896Magnesium AcetateHCID 13334672N-acetoacetylaspartic acid2×

Product 1

HCID 13334674N-acetoacetyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

2.17 parts of N-acetoacetyl-L-aspartic acid, 1.02 parts by volume of acetic anhydride, and 0.014 parts of magnesium acetate were mixed with 40 parts by volume of ethyl acetate and heated at 55±2° C. under nitrogen for 24 hours. 30 parts by volume of methanol was added and the mixture stirred at ambient temperatures for 5 hours. HPLC analysis of the resulting solution showed only 0.5% unreacted N-acetoacetyl-L-aspartic acid.

Sources & evidence

ORD record
ord-aded7f4057e441d5be9e893efb22e00a
Source dataset
uspto-grants-1984_04
Patent number
US04440677

Reaction notes

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