Sodium Hydroxide → 8-Bromo-2'-deoxyadenosine

HRID 2262389Notes

Reaction equation

HRID 2262389 reaction equation
O.[C@@H:2]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1.[Br:20]Br.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>C([O-])(=O)C.[Na+]>[Br:20][C:11]1[N:10]([C:19]2[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=2[N:12]=1)[C@@H:2]1[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 95491722'-Deoxyadenosine monohydrate

Product 1

HCID 965478-Bromo-2'-deoxyadenosineYield 84.8%

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent2×

Procedure

2′-Deoxyadenosine monohydrate (4 g, 15 mmol) was suspended in 75 mL of a sodium acetate buffer solution (pH 4.3). To this suspension, 75 mL of a sodium acetate buffer solution (pH 4.3) containing bromine (0.92 mL, 18 mmol) was dropwise added. The resulting mixture was stirred at room temperature for 2 hours, and then 50 mL of a 5% sodium thiosulfate aqueous solution and then 50 mL of a 2 M sodium hydroxide aqueous solution were added thereto. The given precipitate was collected by filtration and sufficiently washed with water and ethanol to give 8-bromo-2′-deoxyadenosine (4.2 g, yield: 83%).

Workup

  1. additionwas dropwise added
  2. filtrationThe given precipitate was collected by filtration
  3. washsufficiently washed with water and ethanol

Sources & evidence

ORD record
ord-951a2fd0254f42fe9b5037b2ffe67ed8
Source dataset
uspto-grants-2010_12
Patent number
US07851157B1

Reaction notes

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