Triethylamine → Adenosine-5'-carboxylic acid benzyl ester

HRID 27979Notes

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].C(N([CH2:29][CH3:30])CC)C>C(O)C1C=CC=CC=1>[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])[C:30]1[CH:29]=[CH:7][CH:6]=[CH:5][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5 g of adenosine-5'-carboxylic acid methyl ester are suspended in 200 ml of benzyl alcohol, with the addition of 7 g of triethylamine, and the reaction mixture heated to 100° C. for 5 hours, the methyl ester thereby going into solution. After termination of the reaction, the base and excess alcohol are stripped off in a vacuum, the residue is triturated with ether for the removal of traces of amine and solvent and, after filtering off with suction, the product is recrystallized from water. There are thus obtained 3.3 g (53% of theory) of adenosine-5'-carboxylic acid benzyl ester, which has a melting point of 144°-145° C.

Workup

customAfter termination of the reaction
customthe residue is triturated with ether for the removal of traces of amine and solvent
filtrationafter filtering off with suction
customthe product is recrystallized from water

Sources & evidence

ORD record: ord-5dc26da6ef4e49d190035222e3dd59f8
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04224438

Reaction notes

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