Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylmethyl)- → Navuridine

A mixture of 3'-azido-5'-O-trityl-2',3'-dideoxyuridine (63 g, 0.132 mol) and 300 ml of acetic acid (80%) was heated at 95°-100° C. for two hours. The reaction mixture was cooled in an ice-bath and the solid separated was filtered off. The filtrate was evaporated to dryness. The residue was dissolved in a methanol-chloroform mixture and concentrated to a syrup. The residue was purified by flash vacuum chromatography over a silica gel column eluting sequentially with chloroform-methanol (70:1), chloroform-methanol (50:1) and finally chloroform-methanol (30:1), to yield 23 g (70%) of 3'-azido-2',3'-dideoxyuridine.

1. temperaturewas heated at 95°-100° C. for two hours
2. temperatureThe reaction mixture was cooled in an ice-bath
3. customthe solid separated
4. filtrationwas filtered off
5. customThe filtrate was evaporated to dryness
6. dissolutionThe residue was dissolved in a methanol-chloroform mixture
7. concentrationconcentrated to a syrup
8. customThe residue was purified by flash vacuum chromatography over a silica gel column
9. washeluting sequentially with chloroform-methanol (70:1), chloroform-methanol (50:1) and finally chloroform-methanol (30:1)

ORD record

ord-1e1f187b943e4b938696cfd7fe87751f

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05159067