L-Aspartic Acid → N-acetoacetylaspartic acid

HRID 1583893Notes

Reaction equation

HRID 1583893 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[CH2:12]=[C:13]1[O:17][C:15](=[O:16])[CH2:14]1>>[C:15]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])(=[O:16])[CH2:14][C:13]([CH3:12])=[O:17]

Participants

4

Reactant 3

HCID 5960L-Aspartic AcidHCID 12661DiketeneHCID 14798Sodium Hydroxide

Product 1

HCID 13334672N-acetoacetylaspartic acid

Procedure

L-aspartic acid, 13.3. parts, was added to 100 parts by volume of 2N aqueous sodium hydroxide and the resulting solution was cooled to 0°-10° C. in an ice bath. Diketene, 8.4 parts, was added and the resulting two phase mixture was stirred for 2.5 hours at 0°-10° C. The homogeneous solution was washed twice with 100 parts by volume of ether and the aqueous layer was acidified with 16.6 parts by volume of concentrated hydrochloric acid. This solution was extracted three times with 100 parts by volume of ethyl acetate, the combined extracts were dried over sodium sulfate, filtered and the solvent evaporated under vacuum at 25°-30° C. to give 2.3 parts of N-aceto-acetyl-L-aspartic acid, mp 127°-129.5° C.

Workup

  1. temperaturethe resulting solution was cooled to 0°-10° C. in an ice bath
  2. washThe homogeneous solution was washed twice with 100 parts by volume of ether
  3. extractionThis solution was extracted three times with 100 parts by volume of ethyl acetate
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum at 25°-30° C.

Sources & evidence

ORD record
ord-f9d11f78e274404c85b53d4e65d2db68
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

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