Methanesulfonyl chloride → 2,5'-Anhydro-3'-azido-3'-deoxythymidine

HRID 1885520Notes

Reaction equation

HRID 1885520 reaction equation
[N:1]([C@@:4]1(O)[C@@H:8]([CH2:9]O)[O:7][C@@H:6]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].CS(Cl)(=O)=O>N1C=CC=CC=1>[CH3:18][C:17]1[C:15](=[O:16])[N:14]=[C:12]2[N:11]([C@@H:6]3[O:7][C@H:8]([CH2:9][O:13]2)[C@@H:4]([N:1]=[N+:2]=[N-:3])[CH2:5]3)[CH:19]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 21115113HCID 21115113, compound

Product 1

HCID 722082,5'-Anhydro-3'-azido-3'-deoxythymidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 5'-hydroxyl of 3' azidothymidine (3.0 g, 11.2 mMol) was mesylated by the addition of methanesulphonyl chloride (2.7 mL) to a solution of the starting material in dry pyridine (20 mL). The reaction was allowed to proceed at 5° C. for one hour, then poured onto ice water. The precipitate was collected by filtration. The desired product was obtained by reacting the 3'-azido-4'-mesylthymidine obtained from the first step with potassium carbonate (0.78 g, 5.6 mMol) in DMF (75 mL). The reaction was heated in an 80° C. oil bath for six hours, then poured into ice water. The product was extracted from the water with ethyl acetate. The solvent was removed in vacuo and the resultant oil was flash chromatographed on silica gel by elution with CHCl3 :MeOH (9:1 v/v). The product was obtained in low yield.

Workup

  1. additionpoured onto ice water
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ca103d83b5b44e9eba93e083efc9bb7d
Source dataset
uspto-grants-1992_09
Patent number
US05145840

Reaction notes

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