Palmitoyl chloride → 3'-deoxy-3'-fluoro-5'-O-palmitoyl-thymidine

HRID 465302

Reaktionsgleichung

Reaktionsgleichung von HRID 465302
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[F:19][C@@H:20]1[C@@H:24]([CH2:25][OH:26])[O:23][C@@H:22]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:21]1.C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[F:19][C@@H:20]1[C@@H:24]([CH2:25][O:26][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:23][C@@H:22]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:21]1

Komponenten

5

Edukt 3

HCID 8206Palmitoyl chlorideHCID 330393'-FluorothymidineHCID 21584188Chloroform methanol

Produkt 1

HCID 152283303'-deoxy-3'-fluoro-5'-O-palmitoyl-thymidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

At 0° C., 1.2 equivalents of palmitoyl chloride are added to a solution of 3'-deoxy-3'-fluorothymidine in pyridine. The solution is warmed slowly to room temperature. As soon as a thin layer chromatographic control (CHCl3 /methanol=95/5 on silica gel) shows a complete reaction, the solution is poured into ice water. The aqueous phase is decanted, the resulting oil is chromatographed on silica gel with chloroform eluent. The title compound is recovered from the suitable fractions by evaporation of the solvent. M.P. 65°-66° C. (cyclohexane).

Aufarbeitung

  1. customa complete reaction
  2. customThe aqueous phase is decanted
  3. customthe resulting oil is chromatographed on silica gel with chloroform eluent
  4. customThe title compound is recovered from the suitable fractions by evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-6d05020b4ad54e78a4feb53e3d6ecd84
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153180

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