Triphosphate → [1,1-difluoro-2-[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]ethyl]-[hydroxy(phosphonooxy)phosphoryl]oxy-phosphinic acid

HRID 1157350Notes

Reaction equation

HRID 1157350 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][C:16]([P:19]([O:22][P:23]([OH:30])(NP(O)(O)=O)=[O:24])([OH:21])=[O:20])([F:18])[F:17])[CH2:12][CH2:11]2)[CH:3]=1.[O-:31][P:32](OP([O-])([O-])=O)(=[O:34])[O-:33].C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.[O-:92]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].P(=O)([O-])OC1NC=CN=1>>[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][C:16]([P:19]([O:22][P:23]([O:30][P:32]([OH:34])([OH:33])=[O:31])([OH:24])=[O:92])([OH:21])=[O:20])([F:17])[F:18])[CH2:12][CH2:11]2)[CH:3]=1

Participants

5

Reactant 4

HCID 3440921TriphosphateHCID 5279011[[[[1,1-difluoro-2-[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]ethyl]-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]amino]phosphonic acidHCID 21910867Tributyl ammonium pyrophosphateHCID 178527063HCID 178527063, compound

Product 1

HCID 5279009[1,1-difluoro-2-[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]ethyl]-[hydroxy(phosphonooxy)phosphoryl]oxy-phosphinic acid

Procedure

Following the procedure for the compound 63, starting from 102 mg (0.19 mmol) of the product 61 from Step C, using tri(n-butyl)ammonium pyrophosphate (246 mg), after 18 h (25% of the target triphosphate in mixture with 41% of the imidazolyl phosphonate intermediate as judged by LCMS) 12 mg of the titled compound 64 was isolated.

Sources & evidence

ORD record
ord-5e1d8cdf1c1f4710b885a53660769ee1
Source dataset
uspto-grants-2010_10
Patent number
US07807653B2

Reaction notes

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