Reaktion #56256

ord-9c1cae5671d24d828dea955f7fa63f98

Reaktionsgleichung

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
Ausbeute 48.0%

Edukte

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

Reagenzien

Keine

Lösungsmittel

CCCCCCO
n-hexanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04224438uspto-grants-1980_09