Acetic Acid → HCID 86741053, compound

HRID 2290198Notes

Reaction equation

HRID 2290198 reaction equation
OC(O)CCC[C:6](=[N:8][C:9]1[C:10]2[N:11]=[CH:12][N:13]([C:23]=2[N:24]=[CH:25][N:26]=1)[C@H:14]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16])C.CO.O.[C:31]([OH:34])(=[O:33])[CH3:32]>>[OH:33][CH:31]([OH:34])[CH2:32][CH2:6][NH:8][C:9]1[C:10]2[N:11]=[CH:12][N:13]([C:23]=2[N:24]=[CH:25][N:26]=1)[C@H:14]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 86741054HCID 86741054, compound

Product 1

HCID 86741053HCID 86741053, compound

Procedure

The title compound was prepared with material from Example 6, (S)-N6 -[Dihydroxypropylisopropylidene]adenosine (2.3 g, 6 mmol). This was placed in 20% acetic acid in 1:1 methanol:water (100 ml), and stirred at ambient temperature for 22 hours. After removal of solvents, the residue was treated with acetone and the resulting percipitate filtered and dried in vacuo. This was then redissolved in 15% acetic acid, 1:1 water:methanol and stirred another 48 hours. Removal of solvents and vacuum drying at 85° yielded 0.77 g final product. m.p. 231°-5°

Workup

  1. customAfter removal of solvents
  2. additionthe residue was treated with acetone
  3. filtrationthe resulting percipitate filtered
  4. customdried in vacuo
  5. dissolutionThis was then redissolved in 15% acetic acid
  6. customRemoval of solvents and vacuum
  7. customdrying at 85°

Sources & evidence

ORD record
ord-f8192705ccb346ff8fa7745d261fee77
Source dataset
uspto-grants-1986_10
Patent number
US04616003

Reaction notes

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