Floxuridine → 2'-Deoxy-5-fluoro-3-(2-tetrahydrofuranyl)uridine

A 16.5 g quantity of N,O-bis(trimethylsilyl) acetamide was added to a suspension of 5.00 g of 2'-deoxy-5-fluorouridine in 50 ml of dry dichloromethane at room temperature with stirring, and the mixture was stirred for four hours. Then a solution of 4.00 g of 2-acetoxytetrahydrofuran and 1.17 ml of stannic chloride in 10 ml of dry dichloromethane was added and the mixture was stirred for 1.5 hours. Then 8.0 ml of triethylamine was added to neutralize the mixture and the mixture was washed with water. The dichloromethane layer was concentrated and the residue was dissolved in 100 ml of methanol. A 3 ml quantity of acetic acid was added thereto and the mixture was left to stand at 40° C. for 3 hours. The solvent was distilled off and the residue was applied to a silica gel column to conduct gradient elution using chloroform and methanol (up to 4%)-chloroform mixtures, giving 5.25 g of 2'-deoxy-5-fluoro-3-(2-tetrahydrofuranyl)uridine as an oil in a yield of 81.7%.

1. stirringthe mixture was stirred for four hours
2. stirringthe mixture was stirred for 1.5 hours
3. washthe mixture was washed with water
4. concentrationThe dichloromethane layer was concentrated
5. dissolutionthe residue was dissolved in 100 ml of methanol
6. additionA 3 ml quantity of acetic acid was added
7. waitthe mixture was left
8. distillationThe solvent was distilled off
9. washelution

ORDレコード

ord-e997426edcb4409b9375fae517d71f4f

出典データセット

uspto-grants-1989_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04864021