Acetamidomalonic acid diethyl ester → HCID 13105387, compound

HRID 358297Notes

Reaction equation

HRID 358297 reaction equation
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].Br[CH:18]([CH2:24][C:25]([NH2:27])=[O:26])[C:19](OCC)=[O:20]>C(O)C>[C:2]([NH:5][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:24]1[CH2:18][C:19](=[O:20])[NH:27][C:25]1=[O:26])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 5360545SodiumHCID 20449793HCID 20449793, compound

Product 1

HCID 13105387HCID 13105387, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 100 ml of ethanol was dissolved 3.4 g of sodium, and following addition of 32 g of diethyl acetylaminomalonate, the mixture was refluxed for 2 hours. To the reaction mixture was added dropwise a solution of 16.5 g of ethyl 2-bromosuccinamate in ethanol (40 ml) and under stirring the mixture was refluxed for 30 minutes. This reaction mixture was concentrated under reduced pressure, followed by addition of ethyl acetate and water, and stirred. The aqueous layer was separated and the ethyl acetate layer was extracted with water. These aqueous extracts were combined, washed with ethyl acetate, adjusted to pH 1.5 with conc. hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the residue was added ethyl ether and the mixture was allowed to stand in a refrigerator, whereupon crystals separated out. Yield 7.3 g.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturewas refluxed for 30 minutes
  3. concentrationThis reaction mixture was concentrated under reduced pressure
  4. additionfollowed by addition of ethyl acetate and water
  5. stirringstirred
  6. customThe aqueous layer was separated
  7. extractionthe ethyl acetate layer was extracted with water
  8. washwashed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. additionTo the residue was added ethyl ether
  14. customseparated out

Sources & evidence

ORD record
ord-41128d49681e445ebc8d935bdb7f1683
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

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