Cyclohexene → Doxifluridine

HRID 1358067

Reaktionsgleichung

Reaktionsgleichung von HRID 1358067
I[CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[C:14]([F:16])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[C@H:5]([OH:17])[C@@H:4]1[OH:18].C1CCCCC=1.C(N(CC)CC)C>C(O)CCC.[Pd]>[F:16][C:14]1[C:12](=[O:13])[NH:11][C:9](=[O:10])[N:8]([CH:15]=1)[C@@H:6]1[O:7][C@H:3]([CH3:2])[C@@H:4]([OH:18])[C@H:5]1[OH:17]

Komponenten

6

Edukt 3

HCID 8079CyclohexeneHCID 8471TriethylamineHCID 108723875'-Deoxy-5'-iodo-5-fluorouridine

Produkt 1

HCID 18343DoxifluridineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of 10 g (0.026 m) of 5′-deoxy-5′-iodo-5-fluoro uridine, obtained as described in Example 2, step A, in 100 ml of n-butanol, 6 ml of cyclohexene (0.06 m) and 14 ml (0.1 m) of triethylamine are added. The mixture is heated to 60° C. in order to achieve a complete solubilization, then 1.5 g of 5% Pd/C are added thereinto. The suspension is heated at 80° C. for 5 hours, filtered at the same temperature by washing with hot n-butanol and concentrated under vacuum until a residue is obtained, which crystallizes with a mixture of 60 ml of ethanol and 40 ml of isopropanol. Thus, 4.5 g of 5′-deoxy-5-fluorouridine are obtained. M.p.=188÷189° C., purity (HPLC)=99.87% and [α]D=18.35° (c=0.42, H2O).

Aufarbeitung

  1. customobtained
  2. temperatureThe suspension is heated at 80° C. for 5 hours
  3. filtrationfiltered at the same temperature
  4. washby washing with hot n-butanol
  5. concentrationconcentrated under vacuum until a residue
  6. customis obtained
  7. customwhich crystallizes with a mixture of 60 ml of ethanol and 40 ml of isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-20df3c7ac38f4c0db877ff53742f7da8
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593467B2

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