Reacción #56260

ord-628c7d3a1ad94e558bc41b3b4bf34f0f

Ecuación de reacción

COC(=O)C(O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
adenosine-5'-carboxylic acid methyl ester
CC(C)(C)N
tert.-butylamine
CC(C)(C)NC(=O)C(O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
adenosine-5'-carboxylic acid N-tert.-butylamide
Rendimiento 38.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrois obtained
  2. 2
    workup.WAITthe reaction mixture is left
  3. 3
    workup.DISTILLATIONExcess tert.-butylamine is then distilled off
  4. 4
    workup.ADDITIONthe residue is mixed with methanol
  5. 5
    Otroagain evaporated to dryness
  6. 6
    Filtraciónis filtered off with suction
  7. 7
    OtroAfter recrystallizing twice from a little methanol, there

Procedimiento

5 g of adenosine-5'-carboxylic acid methyl ester are heated together with 100 ml of tert.-butylamine on a streambath until a clear solution is obtained and thereafter the reaction mixture is left to stand for 16 hours at ambient temperature. Excess tert.-butylamine is then distilled off and the residue is mixed with methanol, again evaporated to dryness and the solid residue, after slurrying in cold methanol is filtered off with suction. After recrystallizing twice from a little methanol, there are obtained 2.15 g (38% of theory) of adenosine-5'-carboxylic acid N-tert.-butylamide, which melts, with decomposition, at 279°-280° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04224438uspto-grants-1980_09