Sodium Iodide → HCID 67534465, compound

HRID 217108Notes

Reaction equation

HRID 217108 reaction equation
[C:1]([O:9][C@H:10]1[C:14]([F:16])([F:15])[CH:13](OS(C)(=O)=O)[O:12][C@@H:11]1[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-:44]>CC(C)=O>[C:1]([O:9][C@H:10]1[C:14]([F:16])([F:15])[CH:13]([I:44])[O:12][C@@H:11]1[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86630303HCID 86630303, compound2×

Product 1

HCID 67534465HCID 67534465, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(2R,3R)-4,4-difluoro-5-(methylsulfonyloxy)-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate 9 (2 g, 3.37 mmol), acetone (20 mL), and NaI (5 g, 33.56 mmol) were charged into a round bottom flask. The resulting mixture was refluxed for >6 hours. HPLC indicated that all starting material 9 was consumed. The reaction mixture was cooled to ambient temperature and filtered. The solvent was removed in vacuo. The residue was partitioned between dichloromethane (105 mL) and water (65 mL). The aqueous layer was extracted with dichloromethane (30 mL). The combined dichloromethane layers were washed sequentially with a 5% aqueous solution of NaHSO3 (2×30 mL), a 1:1 mixture of water and brine (20 mL), and brine (2×20 mL). The solution was dried over MgSO4, filtered, and concentrated to give 1.68 g of (2R,3R)-4,4-difluoro-5-iodo-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate 10. H1 NMR (CDCl3): δ3.44-3.57 (dd, 2H), 4.41 (m, 1H), 5.60-5.65 (dd, 1H), 6.95 (d, 1H), 7.21-8.15 (m, 20H).

Workup

  1. temperatureThe resulting mixture was refluxed for >6 hours
  2. customwas consumed
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. customThe residue was partitioned between dichloromethane (105 mL) and water (65 mL)
  6. extractionThe aqueous layer was extracted with dichloromethane (30 mL)
  7. washThe combined dichloromethane layers were washed sequentially with a 5% aqueous solution of NaHSO3 (2×30 mL)
  8. additiona 1:1 mixture of water and brine (20 mL), and brine (2×20 mL)
  9. dry with materialThe solution was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-40ef9fab16e241adb111f0d1fca9f633
Source dataset
uspto-grants-2012_06
Patent number
US08193339B2

Reaction notes

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