Acetic Anhydride → N-acetoacetyl-L-aspartic anhydride

HRID 1583903Notes

Reaction equation

HRID 1583903 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(OCCCC)(=O)C.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 7918Acetic AnhydrideHCID 8896Magnesium AcetateHCID 31272Butyl AcetateHCID 13334672N-acetoacetylaspartic acid

Product 1

HCID 13334674N-acetoacetyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

N-acetoacetyl-L-aspartic acid, 21.7 parts, was mixed with 30 parts by volume of n-butyl acetate and 10.7 parts acetic anhydride. A solution of 0.20 parts anhydrous magnesium acetate in 2.0 parts by volume of glacial acetic acid was added and the slurry was stirred for 30 minutes at 25° C. The mixture was stirred for 2.5 hours at 40°-50° C. and then was cooled to 25° C. The solid was collected on a filter under nitrogen, it was rinsed with n-butyl acetate, and then was dried at 0.1 mm to afford 19.3 parts N-acetoacetyl-L-aspartic anhydride.

Workup

  1. stirringThe mixture was stirred for 2.5 hours at 40°-50° C.
  2. temperaturewas cooled to 25° C
  3. customThe solid was collected on
  4. filtrationa filter under nitrogen
  5. washit was rinsed with n-butyl acetate
  6. customwas dried at 0.1 mm

Sources & evidence

ORD record
ord-9391e1980ed04128adc93d938755c4e3
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

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