Sulfuric Acid → Adenosine-5'-carboxylic acid n-hexyl ester

HRID 27978

Reaction equation

HRID 27978 reaction equation
[C@@H:1]1([N:13]2[C:22]3[N:21]=[CH:20][N:19]=[C:17]([NH2:18])[C:16]=3[N:15]=[CH:14]2)[O:12][C@H:6]([CH:7]([C:9]([OH:11])=[O:10])[OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].S(=O)(=O)(O)O.C(N([CH2:33][CH3:34])CC)C>C(O)CCCCC>[CH2:1]([O:10][C:9]([CH:7]([OH:8])[C@H:6]1[O:12][C@@H:1]([N:13]2[C:22]3[N:21]=[CH:20][N:19]=[C:17]([NH2:18])[C:16]=3[N:15]=[CH:14]2)[C@H:2]([OH:3])[C@@H:4]1[OH:5])=[O:11])[CH2:2][CH2:4][CH2:6][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 21117205CID 21117205

Product 1

HCID 22812369Adenosine-5'-carboxylic acid n-hexyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Procedure

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.

Workup

  1. temperatureAfter cooling
  2. waitleft
  3. customthe desired n-hexyl ester and triethylamine sulfate thereby crystallizing out
  4. filtrationAfter filtering off with suction
  5. washthe triethylamine sulfate is washed out with water
  6. customthe remaining ester is recrystallized from methanol

Sources & evidence

ORD record
ord-9c1cae5671d24d828dea955f7fa63f98
Source dataset
uspto-grants-1980_09
Patent number
US04224438

Linked notes

Loading…