Sodium Benzoate → 5'-Benzoyl-2',3'-didehydro-3'-deoxythymidine

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence