N6-(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate → N6-(5-oxo-2-pyrrolidinyl)adenosine

HRID 358011Notes

Reaction equation

HRID 358011 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[C:34]2[N:33]=[CH:32][N:31]=[C:23]([NH:24][CH:25]3[CH2:29][CH2:28][C:27](=[O:30])[NH:26]3)[C:22]=2[N:21]=[CH:20]1)(=O)C>N>[O:30]=[C:27]1[NH:26][CH:25]([NH:24][C:23]2[C:22]3[N:21]=[CH:20][N:19]([C:34]=3[N:33]=[CH:32][N:31]=2)[C@@H:6]2[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]2[OH:4])[CH2:29][CH2:28]1

Participants

3

Reactant 1

HCID 13109688N6-(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate

Product 1

HCID 13145924N6-(5-oxo-2-pyrrolidinyl)adenosineYield 67.9%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To N6 -(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate (2.2 g) was added cold ammonia-saturated methanol (40 ml), and the resulting mixture was allowed to stand in a refrigerator (at 4° C.) overnight. Next morning the solvent was removed at room temperature. To the residue was added a small amount of methanol and the mixture was allowed to stand at room temperature. The resulting precipitate was recovered by filtration and dried to give N6 -(5-oxo-2-pyrrolidinyl)adenosine as crystals (1.098 g).

Workup

  1. customto stand in a refrigerator (at 4° C.) overnight
  2. customNext morning the solvent was removed at room temperature
  3. additionTo the residue was added a small amount of methanol
  4. customto stand at room temperature
  5. filtrationThe resulting precipitate was recovered by filtration
  6. customdried

Sources & evidence

ORD record
ord-09ad0f304203499d8bc4681d29466b0d
Source dataset
uspto-grants-1984_08
Patent number
US04464361

Reaction notes

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