Trifluoroacetic acid → HCID 89668749, compound

HRID 1482376Notes

Reaction equation

HRID 1482376 reaction equation
[C:1](OCC#N)(=[O:5])[CH2:2][CH:3]=[CH2:4].C([N+](CCCC)(CCCC)CCCC)CCC.[P:27]([O:31][CH2:32][C@@H:33]1[C@@H:37]([O:38][P:39]([O:42][CH2:43][C@@H:44]2[C@@H:48]([OH:49])[C@@H:47]([OH:50])[C@H:46]([N:51]3[CH:59]=[N:58][C:57]4[C:52]3=[N:53][CH:54]=[N:55][C:56]=4[NH2:60])[O:45]2)([OH:41])=[O:40])[CH2:36][C@H:35]([N:61]2[CH:66]=[CH:65][C:64]([NH2:67])=[N:63][C:62]2=[O:68])[O:34]1)([OH:30])([OH:29])=[O:28].C(O)(C(F)(F)F)=O>CN(C=O)C>[C:1]([O:49][C@H:48]1[C@@H:47]([OH:50])[C@H:46]([N:51]2[CH:59]=[N:58][C:57]3[C:52]2=[N:53][CH:54]=[N:55][C:56]=3[NH2:60])[O:45][C@@H:44]1[CH2:43][O:42][P:39]([O:38][C@H:37]1[CH2:36][C@H:35]([N:61]2[CH:66]=[CH:65][C:64]([NH2:67])=[N:63][C:62]2=[O:68])[O:34][C@@H:33]1[CH2:32][O:31][P:27]([OH:30])([OH:29])=[O:28])([OH:41])=[O:40])(=[O:5])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 89668765HCID 89668765, compound2×HCID 117735960((2R,3S,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3-(((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)tetrahydrofuran-2-yl)methyl dihydrogenphosphate tetrabutylammonium salt2×

Product 1

HCID 89668749HCID 89668749, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyanomethyl but-3-enoate (Compound 86) (0.050 g, 0.400 mmol) was added to a solution of ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-(((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)tetrahydrofuran-2-yl)methyl dihydrogenphosphate tetrabutylammonium salt (Compound 1h) (0.20 g, 0.150 mmol) in DMF (1.0 ml), and the mixture was stirred at room temperature for 1 hour. A 0.05% aqueous TFA solution was added to the reaction solution, the mixture was lyophilized, and the resulting residue was purified by preparative HPLC (0.05% aqueous TFA solution:acetonitrile) to prepare the title compound 85 (0.010 g, 10%).

Workup

  1. customthe resulting residue was purified by preparative HPLC (0.05% aqueous TFA solution:acetonitrile)
  2. customto prepare the title compound 85 (0.010 g, 10%)

Sources & evidence

ORD record
ord-69a5dcb52aea4b6c85b103d349da58b1
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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