Methanol → 2-Fluoroadenosine

2-Fluoro-2',3',5'-tri-O-acetyladenosine (0.41 g, 10 mmol) was dissolved in a mixture of 1,4-dioxane (7 mL) and water (2 mL) and the solution was cooled in an ice-water bath. 2.5 M NaOH (1.40 mL, 3.5 mmol) was added dropwise with vigorous stirring over a 2 min. period. The resulting bright yellow solution was stirred at 0° C. and monitored by TLC (9:1 Chloroform:methanol). After 2 hours, most of the yellow color had faded and TLC showed no acetylated intermediates remaining. The homogeneous reaction mixture was poured directly onto a column of AG 50-X4 (H+, 100-200 mesh, 10 mL bed volume) ion exchange resin and the column was eluted with several column volumes of 1:1 methanol:water. 2-Fluoroadenosine began to elute immediately, and all fractions which contained 2-fluoroadenosine were concentrated under vacuum to obtain a white partially crystalline solid which was dried overnight at 60° C. under vacuum: 0.20 g (70% yield), mp 220°-227° C. (d). This material was consistent by TLC, IR and UV with an authentic sample of 2-fluoroadenosine.

1. temperaturethe solution was cooled in an ice-water bath
2. stirringThe resulting bright yellow solution was stirred at 0° C.
3. waitAfter 2 hours
4. additionThe homogeneous reaction mixture was poured directly onto a column of AG 50-X4 (H+, 100-200 mesh, 10 mL bed volume) ion exchange resin
5. washthe column was eluted with several column volumes of 1:1 methanol
6. washto elute immediately
7. concentrationwere concentrated under vacuum
8. customto obtain a white partially crystalline solid which
9. customwas dried overnight at 60° C. under vacuum

ORD-Eintrag

ord-3a08d211c00f4206892ee322e4557e2c

Quelldatensatz

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05602246