Methanol → 5-Iodo-5'-O-p-tolylsulfonyl-2'-deoxycytidine

Participants

Reaction Steps

To a suspension of 5-iodo-2'deoxycytidine (17.65g, 50.00 mmol) in 250 ml of dry pyridine at 0° (ice bath) is added p-toluenesulfonyl chloride (11.50g, 60.00 mmol). The reaction mixture is stirred at 0° for 1 h and then stored at 3° in the dark with stirring for an additional 23 h. At the end of the reaction a clear solution is obtained, to which 15 ml of methanol is added. After standing for 30 min, the solvent is removed under diminished pressure at room temperature to afford a syrup which is coevaporated several times with methanol. The residue is triturated with icecooled water to give a crystalline mass which is broken down to the fine particles with a spatula. The solid material is collected by filtration, washed thoroughly with water, a small amount of ice-cooled ethanol, ether, and dried in vacuo to yield 20.24 g (80%) of the desired product.

Provenance & Evidence