Acetic Anhydride → N-acetoacetyl-L-aspartic anhydride

HRID 1583905Notes

Reaction equation

HRID 1583905 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(OCCC)(=O)C.C(OC(=O)C)(=O)C.[O-2].[Mg+2]>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 7997Propyl AcetateHCID 6850729Magnesium monoxideHCID 13334672N-acetoacetylaspartic acid

Product 1

HCID 13334674N-acetoacetyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

N-acetoacetyl-L-aspartic acid, 80.4 parts, was mixed with 111 parts by volume of dry n-propyl acetate and 39.6 parts of acetic anhydride. A solution of 0.207 parts magnesium oxide in 7.4 parts by volume glacial acetic acid was added and the mixture was stirred at 45°-50° C. for 75 minutes. The resulting slurry was cooled to 10° C. and the solid was collected on a filter under nitrogen. The solid was rinsed with n-propyl acetate and dried at 0.1 mm to afford 70.3 parts of N-acetoacetyl-L-aspartic anhydride.

Workup

  1. customthe solid was collected on
  2. filtrationa filter under nitrogen
  3. washThe solid was rinsed with n-propyl acetate
  4. customdried at 0.1 mm

Sources & evidence

ORD record
ord-783df4ebc1e94dc7896691e1fe7a2da8
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

Loading…