Hydrogen Peroxide → HCID 86756695, compound

HRID 1977099Notes

Reaction equation

HRID 1977099 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:12]1[C@H:19]2[C@H:15]([O:16][C:17]([CH3:21])([CH3:20])[O:18]2)[C@@H:14]([CH2:22][OH:23])[O:13]1.[OH-].[K+].[O-:26][Mn](=O)(=O)=O.[K+].OO>O>[NH2:1][C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:12]1[C@H:19]2[C@@H:15]([O:16][C:17]([CH3:20])([CH3:21])[O:18]2)[C@H:14]([C:22]([OH:26])=[O:23])[O:13]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 14999717HCID 14999717, compound

Product 1

HCID 86756695HCID 86756695, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
7.5 °C

Procedure

To a stirred solution of 1.6 g (3.7 mmol) of [(1R,2R,4R,5R)-4-(6-amino-2-iodopurin-9-yl)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl]methan-1-ol (6.6) in 200 mL of H2O was added 0.60 g of KOH and, dropwise, a solution of 1.70 g (10.8 mml) of KMnO4 in 50 mL of H2O. The mixture was set aside in the dark at room temperature for 225 hours. The reaction mixture was then cooled to 5-10° C. and decolorized by a solution of 4 mL of 30% H2O2 in 16 mL of water, while the temperature was maintained under 10° C. using an ice-salt bath. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to about 10 mL and then acidified to pH 4 with 2N HCl. The resulting precipitate was filtered off and washed with ether to yield 6.7 (70%) after drying as a white solid, m.p. 187-190° C. 1H NMR (300 MHz, DMSO-d6) δ 8.11 (s, 1H, H-8), 7.62 (s, 2H, NH2), 7.46 (s, 1H, COOH), 6.22 (s, 1H, H-1′), 5.42 (d, J=5.71 Hz, 1H, H-2′), 5.34 (d, J=6.16 Hz, 1H, H-3′), 4.63 (s, 1H, H-4′), 1.46 and 1.30 (s, 3H, C(CH3)2).

Workup

  1. customdark at room temperature
  2. customfor 225 hours
  3. temperaturewas maintained under 10° C.
  4. filtrationThe mixture was filtered through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure to about 10 mL
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with ether

Sources & evidence

ORD record
ord-4b8c931223ee41158a07110de1b086c8
Source dataset
uspto-grants-2001_05
Patent number
US06232297B1

Reaction notes

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