Sodium Benzoate → 5'-Benzoyl-2',3'-didehydro-3'-deoxythymidine
Reaction equation
[C:1]([O-:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].CS([C@@:15]1(O)[C@:19](S(C)(=O)=O)(O)[C@@H:18]([CH:25](S(C)(=O)=O)[OH:26])[O:17][C@H:16]1[N:31]1[CH:38]=[C:37]([CH3:39])[C:35](=[O:36])[NH:34][C:32]1=[O:33])(=O)=O.Br.CC(O)=O>CN(C=O)C.[Zn]>[C:1]([CH:25]([OH:26])[C@H:18]1[O:17][C@@H:16]([N:31]2[CH:38]=[C:37]([CH3:39])[C:35](=[O:36])[NH:34][C:32]2=[O:33])[CH:15]=[CH:19]1)(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a slurry of powdered sodium benzoate (3.5 g, 24.3 mmol) in DMF (25 ml) at 90° C. was added tris(methanesulfonyl)-5-methyluridine (IX, 5.0 g, 10.2 mmol). The reaction was stirred for 5.5 hours at 90° C. HBr/HOAc (30-32%, 5 ml, 25.1 mmol) was added and the reaction was stirred for one hour. The reaction mixture was cooled to 25° C. and zinc dust (2.0 g, 30.6 mmol) was added. The reaction was stirred for 30 minutes. The excess zinc was removed by filtration and washed with 2×100 ml methanol. To the filtrate was added 100 ml ice-cold water. The resulting slurry was stirred at 0° C. for 30 minutes and then filtered, dried to give 5'-benzoyl-d4T, 2.34 g (71%).
Workup
- stirringthe reaction was stirred for one hour
- temperatureThe reaction mixture was cooled to 25° C.
- stirringThe reaction was stirred for 30 minutes
- customThe excess zinc was removed by filtration
- washwashed with 2×100 ml methanol
- additionTo the filtrate was added 100 ml ice-cold water
- stirringThe resulting slurry was stirred at 0° C. for 30 minutes
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-555023dba2ed4bbdaffb659b9163f9ad
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05672698
Reaction notes
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