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.C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(N(C)C)=O>[C:25]([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:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
15 Grams of 2'-deoxy-5-fluoro uridine (FudR) was dissolved in 45 ml of dimethylacetamide. Thereto was added 9 ml of triethylamine. To the mixture being cooled with ice-water was added 8.6 g of benzoyl chloride and the whole mixture was stirred overnight. The reaction mixture was subjected to filtration. The resulting filtrate was subjected to evaporation to obtain the residue, and water was added to the residue. The aqueous solution was extracted with ethyl acetate, and the organic layer was dried with anhydrous sodium sulfate. The dried ethyl acetate solution was concentrated and the residue was recrystallized from ethanol to obtain the desired compound. The yield was 10.5 g. M.p. 126° to 127° C.
Workup
- filtrationThe reaction mixture was subjected to filtration
- customThe resulting filtrate was subjected to evaporation
- customto obtain the residue, and water
- additionwas added to the residue
- extractionThe aqueous solution was extracted with ethyl acetate
- dry with materialthe organic layer was dried with anhydrous sodium sulfate
- concentrationThe dried ethyl acetate solution was concentrated
- customthe residue was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-e8666096cdf1472fa2c75f3848ee82ba
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886877
Linked notes
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