Reaction #216279

ord-8a72c79e271e4490ac9e4fe591f46403

Reaction equation

Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
5-methyluridine
CS(=O)(=O)Cl
methanesulfonyl chloride
→
Cc1cn([C@@H]2O[C@H](C(O)S(C)(=O)=O)[C@](O)(S(C)(=O)=O)[C@]2(O)S(C)(=O)=O)c(=O)[nH]c1=O
2',3',5'-Tris(methanesulfonyl)-5-methyluridine

Reactants

Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
5-methyluridine
CS(=O)(=O)Cl
methanesulfonyl chloride
—
ice water

Reagents

None

Solvents

c1ccncc1
pyridine

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGwith stirring
  2. 2
    OtherTrimethanesulfonyl-5-methyluridine (2) precipitated
  3. 3
    workup.STIRRINGthe mixture was stirred for 5 min
  4. 4
    FiltrationThe solid product was collected by filtration
  5. 5
    Washwashed with water (3×200 mL)
  6. 6
    Otherdried
  7. 7
    OtherYield

Procedure

To a stirred mixture of 5-methyluridine (12.8 g, 50 mmol) in pyridine (75 mL) at 0° C. was added methanesulfonyl chloride (17.4 mL, 225 mmol). The reaction mixture was stirred at 0° C. for five hours then poured into ice-water (500 mL) with stirring. Trimethanesulfonyl-5-methyluridine (2) precipitated and the mixture was stirred for 5 min. The solid product was collected by filtration and washed with water (3×200 mL) and dried. Yield, 21.6 g, 89%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05466787uspto-grants-1995_11