1-Bromononane → HCID 22877185, compound

HRID 1416720Notes

Reaction equation

HRID 1416720 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 is added 2.25 g of 60% sodium hydride (oil). After one hour, 8.5 ml of 1-bromononane is added. The reaction is stirred for 16 hours. Ice is added and the solution evaporated in vacuo. Water and ethyl acetate are added. The organic phase is separated, dried, and evaporated in vacuo to give a white solid, which is 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 is added
  2. customthe solution evaporated in vacuo
  3. additionWater and ethyl acetate are added
  4. customThe organic phase is separated
  5. customdried
  6. customevaporated in vacuo
  7. customto give a white solid, which
  8. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-5b19e9d31f6d4ecaad3374dd56b6de7f
Source dataset
uspto-grants-1999_06
Patent number
US05914396

Reaction notes

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