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

HRID 466098Notizen

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-4592c04c83384e83ae339a2d7a7436dc
Quelldatensatz: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05155113

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