Sodium Hydroxide → HCID 15485096, compound

HRID 1905367Notes

Reaction equation

HRID 1905367 reaction equation
N[C:2]1[N:3]=[C:4]([NH2:21])[C:5]2[N:6]=[CH:7][N:8]([C:19]=2[N:20]=1)[C@@H:9]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:10]1[O:11][CH3:12].N([O-])=O.[Na+].[OH-].[Na+].[H+].[B-](F)(F)(F)[F:30]>>[F:30][C:2]1[N:3]=[C:4]([NH2:21])[C:5]2[N:6]=[CH:7][N:8]([C:19]=2[N:20]=1)[C@@H:9]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:10]1[O:11][CH3:12]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 28118Tetrafluoroboric acidHCID 99008052-Amino-2'-O-methyladenosineHCID 23668193Sodium Nitrite

Product 1

HCID 15485096HCID 15485096, compoundYield 23%

Conditions

Temperature
-20 °C

Procedure

3 g of 2-amino-2'-O-methyladenosine, the Compound 30 in Example 15, was dissolved in 35 ml of 42% fluoboric acid. 1.3 g/10 ml aqueous solution of sodium nitrite was added to the solution with stirring at -5° C. to -10° C. and stirred for one hour. The reaction mixture was cooled to -20° C. and neutralized by 50% sodium hydroxide aqueous solution. The solution was desalted by hydrophobic column chromatography and crystallized from methanol to give 697 mg of 2-fluoro-2'-O-methyladenosine (Compound 29).

Workup

  1. stirringstirred for one hour
  2. customcrystallized from methanol

Sources & evidence

ORD record
ord-079639ecff604e518fcba85152c8319f
Source dataset
uspto-grants-1989_06
Patent number
US04843066

Reaction notes

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