Water → HCID 86585369, Verbindung

HRID 433874

Reaktionsgleichung

Reaktionsgleichung von HRID 433874
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[C:20](Cl)(=[O:25])[CH2:21][C:22](Cl)=[O:23].[OH2:27]>C(#N)C>[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[C:20]([OH:25])(=[O:6])[CH2:21][C:22]([OH:23])=[O:27]

Komponenten

5

Edukt 3

HCID 962WaterHCID 35370ZidovudineHCID 74269Propanedioyl dichloride

Produkt 1

HCID 86585369HCID 86585369, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

One gram of AZT was dissolved in 30 ml of anhydrous acetonitrile and added dropwise to a solution of 632 mg of malonyl chloride in 20 ml of acetonitrile at 0° C. The reaction mixture was stirred for 2 hours at 0° C. then at 8-10° C. for 4.5 hours. Thin layer chromatography was used to indicate that the reaction was complete. Water (4 ml) was added. Solvents were removed in vacuo and the residue purified by silica gel chromatography eluting with CHCl3:MeOH. Pure product was obtained in a 68% yield.

Aufarbeitung

  1. waitat 8-10° C. for 4.5 hours
  2. customSolvents were removed in vacuo
  3. customthe residue purified by silica gel chromatography
  4. washeluting with CHCl3
  5. customPure product was obtained in a 68% yield

Quellen und Nachweise

ORD-Eintrag
ord-7b4e75d009ce4e7f9b25fb3eb70d387c
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670341B1

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