Acetone → HCID 14999717, compound

HRID 2242469Notes

Reaction equation

HRID 2242469 reaction equation
[I:1][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].Cl(O)(=O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH3:32][C:33]([CH3:35])=O>>[NH2:20][C:4]1[N:3]=[C:2]([I:1])[N:19]=[C:18]2[C:5]=1[N:6]=[CH:7][N:8]2[C@H:9]1[C@H:10]2[C@H:12]([O:13][C:33]([CH3:35])([CH3:32])[O:11]2)[C@@H:14]([CH2:15][OH:16])[O:17]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 24247Perchloric AcidHCID 1696622-Iodoadenosine

Product 1

HCID 14999717HCID 14999717, compoundYield 93%

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-iodoadenosine 1 (10.0 g, 25.4 mmol) in acetone (200 ml) cooled to 0° C. was added dropwise 70% perchloric acid (4.0 mL), resulting in an exotherm of about 5° C. The resultant colorless solution was allowed to warm to room temperature over 30 minutes, then stirred for a further 45 minutes. 1M Na2CO3 (50 mL) was added, resulting in solids precipitating. This was followed by the careful portionwise addition of water (300 mL) with stirring until all solids had dissolved. The mixture was extracted with three portions of CH2Cl2. The combined organics were washed with brine, dried (Na2SO4), filtered, and evaporated to afford Compound 2 (10.26 g, 93%) as a colorless solid. 1H-NMR (600 MHz, DMSO d6): 1.32 (s, 3H), 1.54 (s, 3H), 3.54 (m, 2H), 4.19 (m, 1H), 4.93 (dd, 1H), 5.05 (t, 1H), 5.27 (dd, 1H), 6.05 (d, 1H), 7.74 (bs, 2H), 8.28 (s, 1H); 13C-NMR (150 MHz, DMSO d6): 25.45, 27.08, 85.69, 86.09, 88.44, 92.59, 114.92, 120.39, 142.47, 151.08, 157.20, 173.14. LRMS (ES): m/z=434.0 (M+H, 100%).

Workup

  1. customresulting in an exotherm of about 5° C
  2. temperatureto warm to room temperature over 30 minutes
  3. customresulting in solids
  4. customprecipitating
  5. additionThis was followed by the careful portionwise addition of water (300 mL)
  6. stirringwith stirring until all solids
  7. dissolutionhad dissolved
  8. extractionThe mixture was extracted with three portions of CH2Cl2
  9. washThe combined organics were washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-998afe3297a7493c99f2196b5715a74c
Source dataset
uspto-grants-2010_03
Patent number
US07671191B2

Reaction notes

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