Sodium Nitrate → HCID 178496714, compound

HRID 366841Notes

Reaction equation

HRID 366841 reaction equation
[CH3:1][O:2][C@@H:3]1[C@H:7]([OH:8])[C@@H:6]([CH2:9][OH:10])[O:5][C@H:4]1[N:11]1[C:20]2[N:19]=[CH:18][N:17]=[C:15](N)[C:14]=2[N:13]=[CH:12]1.[N+]([O-])([O-])=[O:22].[Na+]>C(O)(=O)C>[CH3:1][O:2][C@@H:3]1[C@H:7]([OH:8])[C@@H:6]([CH2:9][OH:10])[O:5][C@H:4]1[N:11]1[C:20]2[N:19]=[CH:18][N:17]=[C:15]([OH:22])[C:14]=2[N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 1022132'-O-Methyladenosine2×

Product 1

HCID 178496714HCID 178496714, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Deamination of 2'-O-methyladenosine was accomplished by a modified procedure of Iwai et al., Anomeric 9-D-Glucopyranosyl-adenines and 9-D-Glucopyranosyl-hypozanthines, in Synthetic Procedures in Nucleic Acid Chemistry 135-142 (Zorbach & Tipson eds., Interscience Publishers, New York, N.Y., 1965). To a solution of 2'-O-methyladenosine (6.61 g, 23.5 mmol) dissolved in 4.4% aqueous acetic acid was added 13.1 g sodium nitrate (190 mmol). This reaction solution was stirred 24 hours in a foil covered vessel and thereafter evaporated to dryness in vacuo. The product was desalted with Amberlite XAD-4 resin and recrystallized in methanol. FABMS (glycerol) m/z 284 (MH+).

Workup

  1. customevaporated to dryness in vacuo
  2. customrecrystallized in methanol

Sources & evidence

ORD record
ord-c9fb7f01dd1f489d90ebd2d560328cb0
Source dataset
uspto-grants-2000_10
Patent number
US06130324

Reaction notes

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