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

HRID 838927Notes

Reaction equation

HRID 838927 reaction equation
[I:1][C:2]1[C:3]([NH2:17])=[N: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:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.CO>N1C=CC=CC=1>[I:1][C:2]1[C:3]([NH2:17])=[N:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][O:13][S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[C@@H:9]([OH:10])[CH2:8]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 73974-Toluenesulfonyl chlorideHCID 65050Ibacitabine

Product 1

HCID 228036685-Iodo-5'-O-p-tolylsulfonyl-2'-deoxycytidineYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  1. customstored at 3° in the dark
  2. stirringwith stirring for an additional 23 h
  3. customAt the end of the reaction a clear solution
  4. additionis added
  5. waitAfter standing for 30 min
  6. customthe solvent is removed under diminished pressure at room temperature
  7. customto afford a syrup which
  8. customThe residue is triturated with icecooled water
  9. customto give a crystalline mass which
  10. filtrationThe solid material is collected by filtration
  11. washwashed thoroughly with water
  12. temperaturea small amount of ice-cooled ethanol, ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-cca646b11ee6435787bb93292de2018c
Source dataset
uspto-grants-1978_06
Patent number
US04093715

Reaction notes

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