Diisopropylamine → Doxifluridine

HRID 1358065

Reaktionsgleichung

Reaktionsgleichung von HRID 1358065
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].C(NC(C)C)(C)C>C(O)C.C(O)(C)C.[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 2

HCID 7912DiisopropylamineHCID 108723875'-Deoxy-5'-iodo-5-fluorouridine

Produkt 1

HCID 18343DoxifluridineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a suspension of 20 g (0.053 m) of 5′-deoxy-5′-iodo-5-fluoro uridine in a mixture of 60 ml of ethanol and 40 ml of isopropanol, 15.2 ml (0.108 m) of diisopropylamine are added, then 3 g of 5% Pd/C are added thereinto and the mixture is hydrogenated at about 1-bar pressure for 14 hours. After removal of the catalyst by filtration, the solution is concentrated under vacuum until a solid residue is obtained, which is crystallized with a mixture ethanol/isopropanol=60/40 v/v; after 8 hours the product is filtered, washed with said mixture and dried at 45° C. for 15 hours. Thus, 11,6 g (yield—89% of the theoretical) of 5′-deoxy-5-fluorouridine M.p.=187÷188° C., puritya (HPLC)=99,75% and [α]D=+18.2° (c=0.42, H2O).

Aufarbeitung

  1. additionare added
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. concentrationthe solution is concentrated under vacuum until a solid residue
  5. customis obtained
  6. customwhich is crystallized with a mixture ethanol/isopropanol=60/40 v/v
  7. filtrationafter 8 hours the product is filtered
  8. washwashed
  9. customdried at 45° C. for 15 hours
  10. customof 5′-deoxy-5-fluorouridine M.p.=187÷188° C., puritya (HPLC)=99,75% and [α]D=+18.2° (c=0.42, H2O)

Quellen und Nachweise

ORD-Eintrag
ord-5aeea353a26646c7a2f55d491f8c579e
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593467B2

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