1-Bromononane → HCID 22877185, compound

HRID 1861030Notes

Reaction equation

HRID 1861030 reaction equation
[C@@H:1]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])[C@H:2]1[OH:3].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CN(C)C=O>[CH2:23]([O:3][C@@H:2]1[C@H:4]([OH:5])[C@@H:6]([CH2:7][OH:8])[O:9][C@H:1]1[N:10]1[C:19]2[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=2[N:12]=[CH:11]1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 127421-BromononaneHCID 24758Sodium hydrideHCID 60961Adenosine

Product 1

HCID 22877185HCID 22877185, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g of adenosine in 400 ml of dimethyl formamide was added 2.25 g of 60% sodium hydride (oil). After one hour, 8.5 ml of 1-bromononane was added. The reaction was stirred for 16 hours. Ice was added and the solution evaporated in vacuo. Water and ethyl acetate were added. The organic phase was separated, dried, and evaporated in vacuo to give a white solid, which was recrystallized from ethanol to yield 4.8 g of the title compound, m.p. 143-144° C. analysis for: C19H31N5O4. Calculated: C, 57.99; H, 7.94; N, 1779. Found: C, 58.13; H, 7.93; N, 17.83.

Workup

  1. additionIce was added
  2. customthe solution evaporated in vacuo
  3. additionWater and ethyl acetate were added
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated in vacuo
  7. customto give a white solid, which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e0932fa87acd4bcc912aa87494321063
Source dataset
uspto-grants-2003_03
Patent number
US06531584B1

Reaction notes

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