Methanol, magnesium salt (2:1) → HCID 13145920, compound

HRID 358016Notes

Reaction equation

HRID 358016 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:35]2[N:34]=[CH:33][N:32]=[C:23]([NH:24][C@@H:25]3[CH2:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])[C:22]=2[N:21]=[CH:20]1)(=O)C.C[O-].[Mg+2].C[O-]>CO>[O:31]=[C:26]1[C@H:25]([NH:24][C:23]2[C:22]3[N:21]=[CH:20][N:19]([C:35]=3[N:34]=[CH:33][N:32]=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][C:28](=[O:30])[NH:27]1

Participants

4

Reactant 2

HCID 164537Methanol, magnesium salt (2:1)HCID 131713630HCID 131713630, compound

Product 1

HCID 13145920HCID 13145920, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N6 -[(R)-2,5-dioxo-3-pyrrolidinyl]adenosine 2',3',5'-triacetate (100 mg), magnesium methoxide (24 mg) and methanol (18 ml) was stirred at room temperature for 48 hours. The reaction mixture was then centrifuged (1500 r.p.m.×20 min.) to remove the precipitate formed during the reaction. The supernatant was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography using ethyl acetate-methanol-water (14:2:1) as the eluent. The active fractions were pooled and concentrated under reduced pressure. The residue was dissolved in water and freeze-dried to give N6 -[(R)-2,5-dioxo-3-pyrrolidinyl]adenosine as powders (20.2 mg).

Workup

  1. custom×20 min.) to remove the precipitate
  2. customformed during the reaction
  3. concentrationThe supernatant was concentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. customfreeze-dried

Sources & evidence

ORD record
ord-1c87f47299b04abd881cfce91b025821
Source dataset
uspto-grants-1984_08
Patent number
US04464361

Reaction notes

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