تفاعل #56256

ord-9c1cae5671d24d828dea955f7fa63f98

معادلة التفاعل

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
المردود 48.0%

المتفاعلات

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

الكواشف

لا شيء

المذيبات

CCCCCCO
n-hexanol

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةAfter cooling
  2. 2
    workup.WAITleft
  3. 3
    أخرىthe desired n-hexyl ester and triethylamine sulfate thereby crystallizing out
  4. 4
    ترشيحAfter filtering off with suction
  5. 5
    غسيلthe triethylamine sulfate is washed out with water
  6. 6
    أخرىthe remaining ester is recrystallized from methanol

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04224438uspto-grants-1980_09