Cidofovir → [(2R)-1-(4-amino-2-oxo-pyrimidin-1-yl)-3-hydroxy-propan-2-yl]oxymethylphosphonic acid

HRID 2260332

Reaction equation

HRID 2260332 reaction equation
C1O[C@H]1CO.C(NC1C=CNC(=O)N=1)(=O)C1C=CC=CC=1.[CH:22]1[C:28]([NH2:29])=[N:27][C:25](=[O:26])[N:24]([CH2:30][C@H:31]([O:34][CH2:35][P:36]([OH:39])([OH:38])=[O:37])[CH2:32][OH:33])[CH:23]=1>>[CH:22]1[C:28]([NH2:29])=[N:27][C:25](=[O:26])[N:24]([CH2:30][C@@H:31]([O:34][CH2:35][P:36]([OH:39])([OH:38])=[O:37])[CH2:32][OH:33])[CH:23]=1

Participants

4

Reactant 3

HCID 60613CidofovirHCID 6973630(-)-GlycidolHCID 178522337HCID 178522337, compound

Product 1

HCID 513605[(2R)-1-(4-amino-2-oxo-pyrimidin-1-yl)-3-hydroxy-propan-2-yl]oxymethylphosphonic acid

Procedure

The title compound (R)-HPMPC was prepared from (S)-glycidol (88% ee) and N4 -benzoylcytosine, following the method described for (S)-HPMPC.

Sources & evidence

ORD record
ord-446b43d0cd8444ea817f87830835fae1
Source dataset
uspto-grants-1995_12
Patent number
US05476938

Linked notes

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