Methyl Ethyl Ketone → N-acetoacetyl-L-aspartic anhydride

HRID 1583904Notes

Reaction equation

HRID 1583904 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].CC(=O)CC.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 6569Methyl Ethyl KetoneHCID 7918Acetic AnhydrideHCID 6850729Magnesium monoxideHCID 13334672N-acetoacetylaspartic acid

Product 1

HCID 13334674N-acetoacetyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-acetoacetyl-L-aspartic acid, 21.7 parts, was mixed with 25 parts by volume of 2-butanone and 10.8 parts acetic anhydride. A solution of 0.056 parts magnesium oxide in 2.0 parts by volume of glacial acetic acid was added and the mixture was stirred at room temperature for 90 minutes. The solid was collected on a filter under nitrogen, rinsed with 2-butanone, and dried at 0.1 mm to afford 17.3 parts N-aceto-acetyl-L-aspartic anhydride.

Workup

  1. customThe solid was collected on
  2. filtrationa filter under nitrogen
  3. washrinsed with 2-butanone
  4. customdried at 0.1 mm

Sources & evidence

ORD record
ord-4bc5cf7341a24ba5b56677241d1a0d1c
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

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