Methanesulfonyl chloride → HCID 22873066, compound

HRID 1781575Notes

Reaction equation

HRID 1781575 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[OH:20])(=[O:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[O:20][S:22]([CH3:21])(=[O:24])=[O:23])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 9814370Thymidine acetate

Product 1

HCID 22873066HCID 22873066, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The 5'-O-acetylthymidine obtained in Example 7 was dissolved in 100 ml of pyridine and cooled to 0° C. Then, 11.57 g (2 equivalents) of methanesulfonyl chloride were added thereto. After these were reacted at 0° C. for 1.5 hours, 5.79 g (one equivalent) of methanesulfonyl chloride were added thereto and reacted at 0° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in methylene chloride, and the insoluble substances were removed by filtration. The organic layer was washed with water; aqueous, saturated sodium hydrogencarbonate solution; water; and saturated saline solution in this order, dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain 10.4 g of 5'-O-acetyl-3'-O-methanesulfonylthymidine. The product was used in the next reaction, without being isolated.

Workup

  1. customAfter these were reacted at 0° C. for 1.5 hours
  2. customreacted at 0° C. for 1.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in methylene chloride
  5. customthe insoluble substances were removed by filtration
  6. washThe organic layer was washed with water
  7. dry with materialand saturated saline solution in this order, dried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72f2399edc644c439d5d6ecafa1270b7
Source dataset
uspto-grants-1997_05
Patent number
US05633366

Reaction notes

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