Acetic Acid → Uridine, 2′,5′-dideoxy-2′-fluoro-
Reaction equation
COC1C=CC(C([O:22][C@@H:23]2[C@@H:27]([CH2:28]OC(C3C=CC=CC=3)(C3C=CC(OC)=CC=3)C3C=CC(OC)=CC=3)[O:26][C@@H:25]([N:53]3[CH:60]=[CH:59][C:57](=[O:58])[NH:56][C:54]3=[O:55])[C@@H:24]2[F:61])(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.C(O)(=O)C>CO>[F:61][C@@H:24]1[C@H:23]([OH:22])[C@@H:27]([CH3:28])[O:26][C@H:25]1[N:53]1[CH:60]=[CH:59][C:57](=[O:58])[NH:56][C:54]1=[O:55]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
The residue obtained in the above described (iv) was dissolved in MeOH, 100 mL of 80% acetic acid was then added thereto. After stirring at 80° C. for 6 hours, the reaction solution was concentrated, and dissolved in 150 mL of H2O. Subsequently, extraction and washing were carried out three times with 150 mL each of CHCl3, then the solvent of the aqueous layer was evaporated. The resulting residue was dissolved in 15 mL of chloroform, then isolated and purified by silica gel column chromatography (chloroform: methanol=1:0 to 7:1). The solvent was evaporated to obtain white crystal of the compound(3) (yield: 1.68 g, 6.8 mmol, 58%).
Workup
- customThe residue obtained in the
- concentrationthe reaction solution was concentrated
- dissolutiondissolved in 150 mL of H2O
- extractionSubsequently, extraction
- washwashing
- customthe solvent of the aqueous layer was evaporated
- dissolutionThe resulting residue was dissolved in 15 mL of chloroform
- customisolated
- custompurified by silica gel column chromatography (chloroform: methanol=1:0 to 7:1)
- customThe solvent was evaporated
- customto obtain white crystal of the compound(3) (yield: 1.68 g, 6.8 mmol, 58%)
Sources & evidence
- ORD record
- ord-51822be1f29c4105a525aa4865196d32
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629447B2
Reaction notes
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