Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Floxuridine | HCID 5790 | — |
| Reactant | N-Carbobenzoxy-L-valine | HCID 726987 | — |
| Reactant | Chloroform methanol | HCID 21584188 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 22821017 | HCID 22821017 | 43.7% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04340728 |
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| Source dataset | uspto-grants-1982_07 |
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| ORD ID | ord-91a487d29e7d408b86951eb02b5e5477 |
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| Source note | uspto-grants-1982_07 |
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