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

HRID 358009Notes

Reaction equation

HRID 358009 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[CH:26][N:25]=[C:23]([NH2:24])[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2].C(O[CH:32]1[NH:36][C:35](=[O:37])[CH2:34][CH2:33]1)C>CN(C)C=O>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[C:28]2[N:27]=[CH:26][N:25]=[C:23]([NH:24][CH:32]3[CH2:33][CH2:34][C:35](=[O:37])[NH:36]3)[C:22]=2[N:21]=[CH:20]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 965032',3',5'-tri-O-acetyladenosineHCID 35805555-Ethoxy-2-pyrrolidinone

Product 1

HCID 13109688N6-(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetateYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Adenosine 2',3',5'-triacetate (2.0 g) and 5-ethoxy-2-pyrrolidinone (1.2 g) were stirred in N,N-dimethylformamide (10 ml) at 130° C. overnight. The reaction mixture was distilled to remove the N,N-dimethylformamide and the residue was subjected to silica gel column chromatography using chloroformacetone (5:3) as the eluent. The active fractions were pooled and concentrated under reduced pressure to give N6 -(5-oxo-2-pyrrolidinyl)adenosine 2',3',5'-triacetate as an oil (2.2 g).

Workup

  1. distillationThe reaction mixture was distilled
  2. customto remove the N,N-dimethylformamide
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf2ea343da54445997c69de70ffc7bbe
Source dataset
uspto-grants-1984_08
Patent number
US04464361

Reaction notes

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