HCID 67779805, compound → HCID 10220985, compound

HRID 129711Notes

Reaction equation

HRID 129711 reaction equation
C([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:24]=2[N:25]=[CH:26][N:27]=1)[C@@H:15]1[O:23][C:20](=[CH:21][F:22])[C@@H:18]([OH:19])[C@H:16]1[OH:17])(=O)C1C=CC=CC=1>C(O)C>[F:22]/[CH:21]=[C:20]1/[C@@H:18]([OH:19])[C@@H:16]([OH:17])[C@H:15]([N:14]2[C:24]3[N:25]=[CH:26][N:27]=[C:10]([NH2:9])[C:11]=3[N:12]=[CH:13]2)[O:23]/1

Participants

3

Reactant 1

HCID 67779805HCID 67779805, compound

Product 1

HCID 10220985HCID 10220985, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 83 mg of N6 -benzoyl-4',5'-didehydro-5'-deoxy-5'-fluoroadenosine (lower Rf isomer above) in absolute ethanol, evaporate and redissolve in 6 ml of ethanol. Bubble anhydrous ammonia through the ice cooled solution in a 20 mm×12 cm Carius tube. Seal the tube and remove the ice bath. After 14 hours at room temperature, open the tube and evaporate the solution to give 87 mg of crude product. Triturate in 1 ml of methanol and filter off the solid. Dry the product in vacuo to give 20 mg of the title compound (a white powder, softens at 100°-110° C. and melts at 225°-230° C.).

Workup

  1. customevaporate
  2. dissolutionredissolve in 6 ml of ethanol
  3. customSeal the tube
  4. customremove the ice bath
  5. customevaporate the solution
  6. customto give 87 mg of crude product
  7. customTriturate in 1 ml of methanol
  8. filtrationfilter off the solid
  9. customDry the product in vacuo

Sources & evidence

ORD record
ord-4c492f6f718e4f538d1d3179fa1024b1
Source dataset
uspto-grants-1995_11
Patent number
US05470837

Reaction notes

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