1-Butanol → Adenosine-5'-carboxylic acid n-butyl ester

HRID 27977Notes

Reaction equation

HRID 27977 reaction equation
[CH3:1][O:2][C:3]([CH:5]([OH:23])[C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[C@@H:7]1[OH:22])=[O:4].[CH2:24](O)[CH2:25][CH2:26]C>>[CH2:1]([O:2][C:3]([CH:5]([OH:23])[C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[C@@H:7]1[OH:22])=[O:4])[CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 2631-ButanolHCID 54489690Adenosine-5'-carboxylic acid methyl ester

Product 1

HCID 54542290Adenosine-5'-carboxylic acid n-butyl esterYield 87%

Procedure

5 g of adenosine-5'-carboxylic acid methyl ester are dissolved in 200 ml of n-butanol and, together with 3 g of D-benzedrine, boiled under reflux for 3 hours. The reaction mixture is filtered and the filtrate evaporated in a vacuum. The evaporation residue is triturated with ether, filtered off with suction, again washed with ether and dried. There are thus obtained 5.6 g of adenosine-5'-carboxylic acid n-butyl ester, which has a melting point of 166°-167° C. The yield is 87% of theory. The crude product obtained can be recrystallized from water.

Workup

  1. temperatureunder reflux for 3 hours
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate evaporated in a vacuum
  4. customThe evaporation residue is triturated with ether
  5. filtrationfiltered off with suction
  6. washagain washed with ether
  7. customdried

Sources & evidence

ORD record
ord-63d3a61b3c064c32855ccc8faa7e3ec6
Source dataset
uspto-grants-1980_09
Patent number
US04224438

Reaction notes

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