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Methanol → N-(Ethoxycarbonothioyl)-L-aspartic acid

HRID 127713
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 127713
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[O:12]([CH3:18])[C:13]([S:15]CC)=S.[CH3:19]O>O>[CH2:18]([O:12][C:13]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])=[S:15])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 5960L-Aspartic AcidHCID 14798Sodium HydroxideHCID 12515750Methyl ethyl xanthate

Produkt 1

HCID 53944913N-(Ethoxycarbonothioyl)-L-aspartic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

L-Aspartic acid (19.95 g, 0.150 mol) was suspended in 15 ml of water at 0° C., and 50% sodium hydroxide solution (24 g, 0.30 mol) was added dropwise with stirring. Methyl ethyl xanthate (22.44 g, 0.165 mol) in 15 ml of methanol was then added in one portion. The mixture was heated at 45° C. for 2 hours, cooled to room temperature, and washed with two portions of ethylene dichloride. The ethylene dichloride washes were discarded and the aqueous phase acidified with concentrated hydrochloric acid at 0° C. The solution was saturated with solid sodium chloride and extracted with two portions of ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate and evaporated in vacuo to afford 29.4 g (89%) of white crystalline N-ethoxythiocarbonyl-L-aspartic acid. mp 133° C.; nmr (DMSO-d6) δ1.23 (t, 3H, J=7 Hz), 2.67 (d, 2H, J=6 Hz), 4.37 (q, 2H, J=7 Hz), 4.93 (dt, 1H, J=6 Hz, 8 Hz), 9.26 (d, 1H, J=8 Hz).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washwashed with two portions of ethylene dichloride
  3. customacidified with concentrated hydrochloric acid at 0° C
  4. extractionextracted with two portions of ethyl acetate
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-202369a7eef443ae976c9ed556f237df
Quelldatensatz
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04256897

Notizen zur Reaktion

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