Sodium Iodide → 3-n-Heptanoyloxymethyl-2'-deoxy-5-fluorouridine

HRID 266016Notes

Reaction equation

HRID 266016 reaction equation
[F:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.[I-].[Na+].[C:20]([O:28][CH2:29]Cl)(=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:20]([O:28][CH2:29][N:4]1[C:3](=[O:17])[C:2]([F:1])=[CH:15][N:6]([C@@H:7]2[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]2)[C:5]1=[O:16])(=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 5790FloxuridineHCID 11430Potassium CarbonateHCID 525228Chloromethyl heptanoate

Product 1

HCID 537961473-n-Heptanoyloxymethyl-2'-deoxy-5-fluorouridineYield 61.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 70 ml of acetone was added 4.95 g of 5-fluoro-2'-deoxyuridine and 12 g of sodium iodide. With stirring at room temperature, thereto was added 7.19 g of chloromethyl n-heptanoate and 15 g of anhydrous potassium carbonate. After the mixture was reacted with stirring at room temperature overnight, the obtained mixture was concentrated under reduced pressure. To the concentrate was added 150 ml of ethyl acetate, and then the insoluble matter was separated by filtration. The flitrate was washed with water, saturated aqueous solution of sodium chloride and water successively, followed by concentrating. The obtained concentrate was purified by silica gel column chromatography (eluting solvent: ethyl acetate) to give 4.77 g of 3-n-heptanoyloxymethyl-2'-deoxy-5-fluorouridine in the form of colorless solid matter (yield: 61.1%). The melting point of the obtained solid matter was 104° to 106° C.

Workup

  1. customAfter the mixture was reacted
  2. stirringwith stirring at room temperature overnight
  3. concentrationthe obtained mixture was concentrated under reduced pressure
  4. additionTo the concentrate was added 150 ml of ethyl acetate
  5. customthe insoluble matter was separated by filtration
  6. washThe flitrate was washed with water, saturated aqueous solution of sodium chloride and water successively
  7. concentrationby concentrating
  8. concentrationThe obtained concentrate
  9. customwas purified by silica gel column chromatography (eluting solvent: ethyl acetate)

Sources & evidence

ORD record
ord-2f621f9de6fa47329b4eedc1f08fc68e
Source dataset
uspto-grants-1997_07
Patent number
US05650172

Reaction notes

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