Propionic Acid → 5-amino-1-(2,3,5,-tri-O-propionyl-beta-D-ribofuranosyl)imidazole-4-carboxamide
Reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17].[C:19]([OH:23])(=O)[CH2:20][CH3:21]>>[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][O:15][C:19](=[O:23])[CH2:20][CH3:21])[C@@H:10]([O:11][C:16](=[O:17])[CH2:3][CH3:2])[C@H:8]2[O:9][C:8](=[O:9])[CH2:10][CH3:12])[CH:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17]Participants
Procedure
A method for producing N2 -phenyl-2,6-diaminonebularine, which comprises reacting 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide with a reactive derivative of propionic acid to yield 5-amino-1-(2,3,5,-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carboxamide, dehydrating 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carboxamide to yield 5-amino-4-cyano-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole, treating 5-amino-4-cyano-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole with aqueous ammonia or alkali metal alkoxide to yield 5-amino-1-β-D-ribofuranosyl-4-cyanoimidazole and reacting 5-amino-1-β-D-ribofuranosyl-4-cyanoimidazole with phenylcyanamide in the presence of ammonia to yield N2 -phenyl-2,6-diaminonebularine.
Sources & evidence
- ORD record
- ord-7e3d7bcacb3a4abcadad9d56861d1184
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255565
Reaction notes
Loading…