Acetamidomalonic acid diethyl ester → 2-(Acetylamino)-2-[4-(acetyloxy)butyl]propanedioic acid, diethyl ester

HRID 1720989

Reaktionsgleichung

Reaktionsgleichung von HRID 1720989
[H-].[Na+].[C:3]([NH:6][CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4].[C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)(=[O:20])[CH3:19]>CN(C)C=O>[C:3]([NH:6][C:7]([CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:18](=[O:20])[CH3:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 24758Sodium hydrideHCID 784911-Butanol, 4-bromo-, 1-acetate

Produkt 1

HCID 105444842-(Acetylamino)-2-[4-(acetyloxy)butyl]propanedioic acid, diethyl esterAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A stirred suspension of 95% sodium hydride (60.8 g, 2.532 mol) in anhydrous dimethylformamide (500 ml) under an atmosphere of argon was cooled to 0° C. (ice bath). A solution of diethyl acetamidomalonate (500 g, 2.302 mol) in anhydrous dimethylformamide (1.2 l) was added over a period of 45 minutes while keeping the reaction temperature below 18° C. After the addition was complete, the turbid solution was gradually warmed to room temperature. After stirring for one hour at room temperature, 4-bromobutyl acetate (471.5 g, 2.417 mol) was added. The mixture was then stirred at 59°-60° C. for 18 hours. The resulting slurry was cooled to room temperature, quenched with absolute ethanol (40 ml) and glacial acetic acid (4 ml), stirred for about 15 minutes, poured into a 10% lithium chloride solution and extracted with ethyl acetate (2×3 l). The combined ethyl acetate extracts were washed with 10% lithium chloride (3×3 l), dried (anhydrous sodium sulfate), and evaporated in vacuo to give 750 g of title product as an oil.

Aufarbeitung

  1. customthe reaction temperature below 18° C
  2. additionAfter the addition
  3. temperaturethe turbid solution was gradually warmed to room temperature
  4. stirringThe mixture was then stirred at 59°-60° C. for 18 hours
  5. temperatureThe resulting slurry was cooled to room temperature
  6. customquenched with absolute ethanol (40 ml) and glacial acetic acid (4 ml)
  7. stirringstirred for about 15 minutes
  8. additionpoured into a 10% lithium chloride solution
  9. extractionextracted with ethyl acetate (2×3 l)
  10. washThe combined ethyl acetate extracts were washed with 10% lithium chloride (3×3 l)
  11. dry with materialdried (anhydrous sodium sulfate)
  12. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee5a19737515474980c8e6774dd31ae7
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05508272

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