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Water → HCID 12764079, Verbindung

HRID 2083837
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2083837
FC(F)(F)C(O)=O.[CH2:8]([O:15][CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[NH2:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[O-2].[Mg+2].[CH3:25][O:26][C:27]1[CH:39]=[CH:38][C:30]([CH2:31][O:32][C:33](N=[N+]=[N-])=[O:34])=[CH:29][CH:28]=1>O1CCOCC1>[CH3:25][O:26][C:27]1[CH:39]=[CH:38][C:30]([CH2:31][O:32][C:33]([NH:18][C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:34])=[CH:29][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 1175214-Methoxybenzyl azidoformateHCID 6850729Magnesium monoxideHCID 131711089HCID 131711089, Verbindung

Produkt 1

HCID 12764079HCID 12764079, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

O-Benzyl-L-serine trifluoroacetic acid salt, 3.09 g. in 20 ml. of water containing 0.8 g. of magnesium oxide is treated with 2.28 g. of p-methoxybenzyloxycarbonyl azide in 20 ml. of dioxane. The mixture is stirred at room temperature for four days. It is then filtered and the filtrate diluted with ethyl acetate and the solution washed with cold 0.2 N hydrochloric acid and with saturated sodium chloride solution. The ethyl acetate solution is dried and evaporated to an oil. The crude product is triturated with isopropyl ether and stored in the cold to yield crystalline material. Separation by filtration gives 1.75 g., mp. 70°-72° C. This product is recrystallized from aqueous ethanol to give 1.54 g. and is again recrystallized from ethyl acetate-hexane to yield 1.25 g. of the above named product, mp. 72°-73° C.

Aufarbeitung

  1. filtrationIt is then filtered
  2. additionthe filtrate diluted with ethyl acetate
  3. washthe solution washed with cold 0.2 N hydrochloric acid and with saturated sodium chloride solution
  4. dry with materialThe ethyl acetate solution is dried
  5. customevaporated to an oil
  6. customThe crude product is triturated with isopropyl ether
  7. customto yield crystalline material
  8. customSeparation
  9. filtrationby filtration
  10. customgives 1.75 g
  11. customThis product is recrystallized from aqueous ethanol
  12. customto give 1.54 g
  13. customand is again recrystallized from ethyl acetate-hexane
  14. customto yield 1.25 g

Quellen und Nachweise

ORD-Eintrag
ord-c840487de34b484dbe9238c038f036e7
Quelldatensatz
uspto-grants-1978_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04086219

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