Acetamidomalonic acid diethyl ester → HCID 13105387, compound

HRID 358296Notes

Reaction equation

HRID 358296 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]([CH2:23][C:24]([NH2:26])=[O:25])[C:19](OC)=[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:23]1[CH2:18][C:19](=[O:20])[NH:26][C:24]1=[O:25])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 5360545SodiumHCID 23364176HCID 23364176, compound

Product 1

HCID 13105387HCID 13105387, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 1 l of ethanol was dissolved 31.6 g of sodium, and following addition of 300 g of diethyl acetylaminomalonate at room temperature, the mixture was stirred for 2 hours. To the reaction mixture, a solution of 144.5 g of methyl 2-bromosuccinamate in ethanol (350 ml) was added dropwise under ice-cooling and the mixture was stirred under ice-cooling for one hour and then at room temperature for an additional one hour. This reaction mixture was concentrated under reduced pressure, followed by addition of 1 l portions of water and ethyl acetate, and stirred. The aqueous layer was separated and the ethyl acetate layer was further extracted with 500 ml of water. These aqueous layers were combined, washed with 1 l of ethyl acetate, adjusted to pH 1.5 with conc. hydrochloric acid and allowed to stand in a refrigerator. The resultant crystals were collected by filtration, washed with water and dried under reduced pressure. Yield 140 g.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for one hour
  4. waitat room temperature for an additional one hour
  5. concentrationThis reaction mixture was concentrated under reduced pressure
  6. additionfollowed by addition of 1 l portions of water and ethyl acetate
  7. stirringstirred
  8. customThe aqueous layer was separated
  9. extractionthe ethyl acetate layer was further extracted with 500 ml of water
  10. washwashed with 1 l of ethyl acetate
  11. filtrationThe resultant crystals were collected by filtration
  12. washwashed with water
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-f576bbad7f864fecb68afd4592c4b1de
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

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