Floxuridine → HCID 22821017, compound

HRID 1759382Notes

Reaction equation

HRID 1759382 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.[CH2:18]([O:25][C:26]([NH:28][C@H:29]([C:33](O)=[O:34])[CH:30]([CH3:32])[CH3:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[CH2:18]([O:25][C:26]([NH:28][C@H:29]([C:33]([O:13][CH2:12][C@H:11]1[O:14][C@@H:7]([N:6]2[CH:15]=[C:2]([F:1])[C:3](=[O:17])[NH:4][C:5]2=[O:16])[CH2:8][C@@H:9]1[OH:10])=[O:34])[CH:30]([CH3:32])[CH3:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 5790FloxuridineHCID 726987N-Carbobenzoxy-L-valineHCID 21584188Chloroform methanol

Product 1

HCID 22821017HCID 22821017, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
-10 °C

Procedure

In pyridine (20 ml) was dissolved 2.00 g (8.12 m-mol) of 2'-deoxy-5-fluorouridine, and the solution was cooled to -10° C. To this solution was added a solution of 2.05 g (8.16 m-mol) of N-benzyloxycarbonylvaline and 2.45 g (8.11 m-mol) of TPS in pyridine (20 ml), and the mixture was allowed to stand for 2 days under cooling (about 5° C.). The solvent was distilled off under reduced pressure from the reaction mixture and the residue was subjected twice to silica gel column chromatography [column size: 3.0×10 cm; developing solvent: CHCl3 -CH3OH (98:2)] under the same operation conditions whereby 1.70 g (yield: 43.7%) of 5'-O-(N-benzyloxycarbonylvalyl)-2'-deoxy-5-fluorouridine was obtained as amorphous powders.

Workup

  1. temperatureunder cooling (about 5° C.)
  2. distillationThe solvent was distilled off under reduced pressure from the reaction mixture

Sources & evidence

ORD record
ord-91a487d29e7d408b86951eb02b5e5477
Source dataset
uspto-grants-1982_07
Patent number
US04340728

Reaction notes

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