Ammonia → HCID 13145920, compound

HRID 358015Notes

Reaction equation

HRID 358015 reaction equation
N.C([O:5][C@@H:6]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16]C(=O)C)[O:8][C@H:7]1[N:20]1[C:36]2[N:35]=[CH:34][N:33]=[C:24]([NH:25][C@@H:26]3[CH2:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])[C:23]=2[N:22]=[CH:21]1)(=O)C>>[O:32]=[C:27]1[C@H:26]([NH:25][C:24]2[C:23]3[N:22]=[CH:21][N:20]([C:36]=3[N:35]=[CH:34][N:33]=2)[C@@H:7]2[O:8][C@H:9]([CH2:15][OH:16])[C@@H:10]([OH:11])[C@H:6]2[OH:5])[CH2:30][C:29](=[O:31])[NH:28]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 131713630HCID 131713630, compound

Product 1

HCID 13145920HCID 13145920, compoundYield 30.8%

Procedure

Cold ammonia-saturated methanol (7 ml) was added to N6 -[(R)-2,5-dioxo-3-pyrrolidinyl]adenosine 2',3',5'-triacetate (300 mg) and the mixture was allowed to stand in a refrigerator overnight. Next morning it was concentrated under reduced pressure and the residue was subjected to high performance liquid chromatography on silica gel using chloroform-methanol-water (65:35:10) as the eluent to give a first fraction A and a second fraction B. The second fraction was concentrated under reduced pressure and the residue was freeze-dried to give N6 -[(R)-2,5-dioxo-3-pyrrolidinyl]adenosine as colorless powders (68.6 mg).

Workup

  1. customto stand in a refrigerator overnight
  2. concentrationNext morning it was concentrated under reduced pressure
  3. customto give a first fraction A
  4. concentrationThe second fraction was concentrated under reduced pressure
  5. customthe residue was freeze-dried

Sources & evidence

ORD record
ord-3b858467f0004e6d892b7f84dd6b5fe2
Source dataset
uspto-grants-1984_08
Patent number
US04464361

Reaction notes

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