Methanesulfonyl chloride → HCID 22851615, compound

HRID 1033287Notes

Reaction equation

HRID 1033287 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[C@@H:7]1[Br:22])(=[O:3])[CH3:2].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[S:24]([O:21][C@@H:8]1[C@H:7]([Br:22])[C@@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:10][C@H:9]1[N:11]1[C:20]2[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=2[N:13]=[CH:12]1)([CH3:23])(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12081666HCID 12081666, compound

Product 1

HCID 22851615HCID 22851615, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 1 g (2.7 mmols) of 5'-O-acetyl-3'-deoxy-3'-bromoadenosine was added to 10 ml of pyridine, 340 mg (1.1 eq.) of methanesulfonyl chloride was added to the mixture. The mixture was stirred at room temperature for 30 minutes and pyridine was distilled off under reduced pressure. The residue was added to 30 ml of water followed by extraction twice with 30 ml of chloroform. After the organic solvent was washed with water and then dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to give 1.09 g (yield, 90%) of 2'-O-mesyl-5'-O-acetyl-3'-deoxy-3'-bromoadenosine.

Workup

  1. additionwas added to the mixture
  2. distillationpyridine was distilled off under reduced pressure
  3. additionThe residue was added to 30 ml of water
  4. extractionfollowed by extraction twice with 30 ml of chloroform
  5. washAfter the organic solvent was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-043f0fb5557e47c6b01699a6d97a5264
Source dataset
uspto-grants-1994_05
Patent number
US05310895

Reaction notes

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