Ammonium fluoride → 3'-Fluorothymidine

HRID 374078

Reaction equation

HRID 374078 reaction equation
S([C@@:5]1(O)[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:12]2[CH:20]=[C:18]([CH3:19])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:6]1)(C)(=O)=O.CC1C(=O)N=C2N([C@@H]3O[C@H](CO)[C@@H](O2)C3)C=1.[FH:38].[K].[F-].[NH4+]>C(O)CO>[F:38][C@@H:5]1[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:12]2[CH:20]=[C:18]([CH3:19])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:6]1

Participants

6

Reactant 4

HCID 25516Ammonium fluorideHCID 69157522,3'-AnhydrothymidineHCID 53443437Potassium fluoride, 99%, spray-driedHCID 53914209HCID 53914209, compound

Product 1

HCID 330393'-FluorothymidineYield 10%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

3'-Mesylthymidine or 2,3'-anhydrothymidine is allowed to react with potassium hydrogen fluoride or ammonium fluoride in ethylene glycol at 191° C. for 10 to 90 minutes, thus giving 3'-deoxy-3'-fluorothymidine (yield: 10 to 14%) [Japanese Patent Publication No. 10472 (1973)].

Sources & evidence

ORD record
ord-1691f48da1a64b31970d925a16ff228d
Source dataset
uspto-grants-1992_11
Patent number
US05166327

Linked notes

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