Triethylamine → 5'-O-acetyl-3-(4-chlorobenzoyl)-3'-O-(4-chlorobenzyl)-2'-deoxy-5-fluorouridine

HRID 1607333Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][O:7][C@@H:8]2[C@@H:12]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[O:11][C@@H:10]([N:18]3[CH:25]=[C:24]([F:26])[C:22](=[O:23])[NH:21][C:19]3=[O:20])[CH2:9]2)=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1.C(N(CC)CC)C>O1CCOCC1>[C:15]([O:14][CH2:13][C@H:12]1[O:11][C@@H:10]([N:18]2[CH:25]=[C:24]([F:26])[C:22](=[O:23])[N:21]([C:34](=[O:35])[C:33]3[CH:37]=[CH:38][C:30]([Cl:29])=[CH:31][CH:32]=3)[C:19]2=[O:20])[CH2:9][C@@H:8]1[O:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:28][CH:27]=1)(=[O:17])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

To a solution of 0.30 g of 3'-O-(4-chlorobenzyl)-5'-O-acetyl-2'-deoxy-5-fluorouridine in 30 ml of dioxane were added 0.38 g of 4-chlorobenzoyl chloride and 0.61 ml of triethylamine, and the mixture was stirred at 40° C. for 3 hours. The insolubles were removed by filtration, and the residue was dissolved in 50 ml of ethyl acetate. The solution was washed with water and dried. The ethyl acetate was distilled off, and the residue was placed on a silica gel column and eluted with chloroform-n-hexane (3:2), thereby producing 0.33 g of the title compound in a yield of 82%.

Aufarbeitung

customThe insolubles were removed by filtration
dissolutionthe residue was dissolved in 50 ml of ethyl acetate
washThe solution was washed with water
customdried
distillationThe ethyl acetate was distilled off
washeluted with chloroform-n-hexane (3:2)

Quellen und Nachweise

ORD-Eintrag: ord-e1d2f9c21fdf414faacad3f46a1b7353
Quelldatensatz: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04864021

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