四氧化硫 → Adenosine-5'-carboxylic acid n-hexyl ester

HRID 27978

反应方程式

HRID 27978 反应方程式
[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]

参与物

5

反应物 3

HCID 1118四氧化硫HCID 8471三乙胺HCID 21117205CID 21117205

产物 1

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

试剂、催化剂与溶剂 1

HCID 8103正己醇溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-9c1cae5671d24d828dea955f7fa63f98
来源数据集
uspto-grants-1980_09
专利号
US04224438

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