Acetone → 3',5'-DI-O-Mesylthymidine

HRID 1735934Notes

Reaction equation

HRID 1735934 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.CC(C)=O.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>O>[CH3:22][S:23]([O:4][C@@H:3]1[C@@H:5]([CH2:6][O:7][S:23]([CH3:22])(=[O:25])=[O:24])[O:8][C@@H:1]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5789ThymidineHCID 31297Methanesulfonyl chloride

Product 1

HCID 105729323',5'-DI-O-MesylthymidineYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dry, round-bottom flask purged with nitrogen was added thymidine (10.0 g, 0.0412 mole) and acetone (30 mL). The slurry was stirred and 3, 5-lutidine (17.7 g, 0.165 mole) was added. Then, methanesulfonyl chloride (13.8 g, 0.124 mole) was added over ten minutes with the temperature rising to 40° C. After 45 minutes, the reaction was complete and the thick slurry was diluted with 150 mL of water. The slurry was stirred for 25° C. for 30 minutes, and then cooled at 0°-5° C. for 30 minutes. The solids were collected, washed with water (80 mL) and isopropanol (40 mL), then dried to give 16.1 g (98.2%) of the title compound.

Workup

  1. customTo a dry, round-bottom flask purged with nitrogen
  2. customrising to 40° C
  3. stirringThe slurry was stirred for 25° C. for 30 minutes
  4. temperaturecooled at 0°-5° C. for 30 minutes
  5. customThe solids were collected
  6. washwashed with water (80 mL) and isopropanol (40 mL)
  7. customdried

Sources & evidence

ORD record
ord-3d861fa7dfe74f108757117e95863dc2
Source dataset
uspto-grants-1996_07
Patent number
US05539099

Reaction notes

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