Hydrochloric Acid → Uridine, 3'-azido-5-chloro-2',3'-dideoxy-

Temperatur

0 °C

3'-Azido-2',3'-dideoxyuridine (0.25 g; 1 mMol) was dissolved in 2 mL dry dimethylacetamide (DMAC), cooled to 0° C. and 2 mL of 0.5M HCl in DMAC was added. m-Chloroperbenzoic acid (0.277 g; 1.6 mMol) was added in two portions over ten minutes and the mixture was allowed to come to ambient temperature. After two hours, 4 mL H2O was added and the solution filtered. The aqueous DMAC solution was extracted with Et2O (3×3 mL) and the Et2O was evaporated in vacuo to an oil which was applied to a silica gel column. Elution with CHCl3MeOH (15:1 v/v), combination of the appropriate fractions and evaporation in vacuo yielded an oil which was crystallized from Et2O to give 58.5 mg (0.2 mMol, 20%): mp=169°-170° C.

1. customto come to ambient temperature
2. filtrationthe solution filtered
3. extractionThe aqueous DMAC solution was extracted with Et2O (3×3 mL)
4. customthe Et2O was evaporated in vacuo to an oil which
5. washElution
6. customwith CHCl3MeOH (15:1 v/v), combination of the appropriate fractions and evaporation in vacuo
7. customyielded an oil which
8. customwas crystallized from Et2O
9. customto give 58.5 mg (0.2 mMol, 20%)

ORD-Eintrag

ord-d1b2c4078cba42f59a0978528ea2b497

Quelldatensatz

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05064946