1,1'-Carbonyldiimidazole → 5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2',3' dideoxyuridine-5'-triphosphate
Reaction equation
[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[CH:19]=[C:18]([CH2:20][C:21]#[C:22][CH2:23][O:24][CH2:25][CH2:26][NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:9][CH2:8]1)([OH:4])([OH:3])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[O-:46][P:47]([O:50][P:51]([O-])([O-:53])=[O:52])(=[O:49])[O-:48].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>>[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[CH:19]=[C:18]([CH2:20][C:21]#[C:22][CH2:23][O:24][CH2:25][CH2:26][NH:27][C:28](=[O:33])[C:29]([F:30])([F:31])[F:32])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:9][CH2:8]1)([O:3][P:51]([O:50][P:47]([OH:49])([OH:48])=[O:46])([OH:53])=[O:52])(=[O:4])[OH:2]Participants
Reactant 3
Product 1
Procedure
Without being limiting in any way, monophosphate (6) can optionally be formed by treatment of 5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2′,3′dideoxyuridine (5) with, for example, POCl3. 5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2′,3′-dideoxyuridine-5′-monophosphate (6) can then optionally be treated with, for example, carbonyldiimidazole (CDI) followed by tetrabutylammonium pyrophosphate (TBAPP) under appropriate conditions to form 5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2′,3′-dideoxyuridine-5′-triphosphate (7). It will be recognized by one of skill in the art that conversion of 5-(4-(N-trifluoroacetyl-2-aminoethoxy)but-2-yn-1-yl)-2′,3′dideoxyuridine (5) to triphosphate (7) can be accomplished by any method known in the art.
Sources & evidence
- ORD record
- ord-eb034e572a3240ca89df4f3570f74beb
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998706B2
Reaction notes
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