Water → 5'-Benzoyl-2',3'-didehydro-3'-deoxythymidine

HRID 975187Notes

Reaction equation

HRID 975187 reaction equation
CS([CH:5]([OH:20])[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])[CH:8]=[CH:7]1)(=O)=O.[C:21]([O-])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+].O>CN(C=O)C>[C:21]([CH:5]([OH:20])[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])[CH:8]=[CH:7]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517055Sodium BenzoateHCID 675752975'-Methanesulfonyl-2',3'-didehydro-3'-deoxythymidine

Product 1

HCID 676362075'-Benzoyl-2',3'-didehydro-3'-deoxythymidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5'-mesyl-d4T (6, 0.4 g) in 6 ml of DMF was added powdered sodium benzoate (0.24 g). The reaction was stirred at 100° C. for 6 hours. After cooling, water (30 ml) was added. The resulting precipitate was filtered, washed with 2×5 ml water and dried to give 5'-benzoly-d4T (7'), 0.04 g (91%).

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with 2×5 ml water
  4. customdried
  5. customto give 5'-benzoly-d4T (7'), 0.04 g (91%)

Sources & evidence

ORD record
ord-cfb43a28daef4a9488e17da1b7a33d7b
Source dataset
uspto-grants-1997_03
Patent number
US05608049

Reaction notes

Loading…