Reacción #56256

ord-9c1cae5671d24d828dea955f7fa63f98

Ecuación de reacción

Nc1ncnc2c1ncn2[C@@H]1O[C@H](C(O)C(=O)O)[C@@H](O)[C@H]1O
adenosine-5'-carboxylic acid
O=S(=O)(O)O
sulfuric acid
CCN(CC)CC
triethylamine
→
CCCCCCOC(=O)C(O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O
adenosine-5'-carboxylic acid n-hexyl ester
Rendimiento 48.0%

Reactantes

Nc1ncnc2c1ncn2[C@@H]1O[C@H](C(O)C(=O)O)[C@@H](O)[C@H]1O
adenosine-5'-carboxylic acid
O=S(=O)(O)O
sulfuric acid
CCN(CC)CC
triethylamine

Reactivos

Ninguno

Disolventes

CCCCCCO
n-hexanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling
  2. 2
    workup.WAITleft
  3. 3
    Otrothe desired n-hexyl ester and triethylamine sulfate thereby crystallizing out
  4. 4
    FiltraciónAfter filtering off with suction
  5. 5
    Lavadothe triethylamine sulfate is washed out with water
  6. 6
    Otrothe remaining ester is recrystallized from methanol

Procedimiento

5 g of adenosine-5'-carboxylic acid are dissolved in 200 ml of n-hexanol and 2 ml of concentrated sulfuric acid and heated to 100° C. for 3 hours. After cooling, the reaction mixture is neutralized with triethylamine and left to stand overnight, the desired n-hexyl ester and triethylamine sulfate thereby crystallizing out. After filtering off with suction, the triethylamine sulfate is washed out with water and the remaining ester is recrystallized from methanol. There are obtained 3.1 g (48% of theory) of adenosine-5'-carboxylic acid n-hexyl ester, which has a melting point of 145°-147° C.

Fuente

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