Triethyl Phosphate → Fludarabine Phosphate

HRID 1451116

Reaction equation

HRID 1451116 reaction equation
[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][C:13]([F:20])=[N:14][C:15]=3[NH2:19])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].P(Cl)(Cl)(Cl)=O.C([O:28][P:29](OCC)([O:31]CC)=[O:30])C.COP(OC)(OC)=O>O>[CH:18]1[N:10]([C@@H:1]2[O:7][C@H:6]([CH2:8][O:9][P:29]([OH:31])([OH:30])=[O:28])[C@@H:4]([OH:5])[C@@H:2]2[OH:3])[C:11]2[C:16](=[C:15]([NH2:19])[N:14]=[C:13]([F:20])[N:12]=2)[N:17]=1

Participants

6

Reactant 4

HCID 6535Triethyl PhosphateHCID 10541Trimethyl PhosphateHCID 24813Phosphorus oxychlorideHCID 657237Fludarabine

Product 1

HCID 30751Fludarabine Phosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorylation: The product from step (e) is mixed with phosphorous oxychloride in an alkyl phosphate such as triethylphosphate, or trimethylphosphate, followed by hydrolysis in water to yield the prodrug 9-β-D-arabinofuranosyl-2-fluoroadenine-5'-phosphate or fludarabine phosphate.

Sources & evidence

ORD record
ord-3d182ccd67e644cba57efc186652ac7e
Source dataset
uspto-grants-1997_02
Patent number
US05602246

Linked notes

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