Methanol → Floxuridine

HRID 2050593Notes

Reaction equation

HRID 2050593 reaction equation
[OH-].[Na+].O.CO.C([C@@:9]1([OH:28])[C@@H:13]([CH:14](C(=O)C)[OH:15])[O:12][C@@H:11]([N:19]2[CH:26]=[C:25]([F:27])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:10]1)(=O)C>C(O)(=O)C>[F:27][C:25]1[C:23](=[O:24])[NH:22][C:20](=[O:21])[N:19]([CH:26]=1)[C@@H:11]1[O:12][C@H:13]([CH2:14][OH:15])[C@@H:9]([OH:28])[CH2:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67918945HCID 67918945, compound

Product 1

HCID 5790FloxuridineYield 78.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 15.55 g (0.389 mol) of sodium hydroxide in 200 ml of ino-exchanged water was mixed with 500 ml of methanol and cooled with ice. Then 42.18 g (0.128 mol) of 2'-deoxy-3',5'-diacetyl-5-fluorouridine (R is CH3 in the general formula (I)) was added to the solution under stirring, and stirring was continued at room temperature for 3.5 hr. As a result the reaction liquid became a clear solution. Then 20 g of acetic acid was added to the reaction liquid for neutralization, and the liquid was concentrated under reduced pressure. The solid residue was dissolved by adding 500 ml of water, followed by addition of 100 ml of a cation-exchange resin (IR 120-B), and the solution was left to stand for 1 hr. Then the resin was filtered out, and the addition of the cation-exchange resin and the subsequent treatment were repeated. After that the filtrate was concentrated and dried under reduced pressure. As the result a white solid was obtained. This solid product was recrystallized from ethanol to thereby obtain 24.80 g (yield 78.9%) of 2'-deoxy-5-fluorouridine. The melting point of this product was 149.5°-150.5° C., and the specific rotary power [α]D25 was +37.3° (C=1.06, H2O).

Workup

  1. temperaturecooled with ice
  2. additionwas added to the solution
  3. stirringstirring
  4. customAs a result
  5. customthe reaction liquid
  6. concentrationthe liquid was concentrated under reduced pressure
  7. dissolutionThe solid residue was dissolved
  8. additionby adding 500 ml of water
  9. additionfollowed by addition of 100 ml of a cation-exchange resin (IR 120-B)
  10. waitthe solution was left
  11. waitto stand for 1 hr
  12. filtrationThen the resin was filtered out
  13. additionthe addition of the cation-exchange resin
  14. concentrationAfter that the filtrate was concentrated
  15. customdried under reduced pressure
  16. customAs the result a white solid
  17. customwas obtained
  18. customThis solid product was recrystallized from ethanol

Sources & evidence

ORD record
ord-1a3e3ca9fe434589902b1f36239c1235
Source dataset
uspto-grants-1991_05
Patent number
US05013828

Reaction notes

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