Sodium Iodide → HCID 178517875, compound

HRID 227153Notes

Reaction equation

HRID 227153 reaction equation
C([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[NH:19][C:18](=[O:20])[N:17]([C@H:21]([C:29]3[NH:33][C:32]4[CH:34]=[CH:35][C:36]([I:38])=[CH:37][C:31]=4[N:30]=3)[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]2=[O:39])=[CH:11][CH:10]=1)(C)(C)C.ClCCl.C(#N)C.[I-].[Na+].Cl[Si](C)(C)C>C(OCC)(=O)C>[OH:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]2[NH:19][C:18](=[O:20])[N:17]([C@H:21]([C:29]3[NH:33][C:32]4[CH:34]=[CH:35][C:36]([I:38])=[CH:37][C:31]=4[N:30]=3)[CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:16]2=[O:39])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 21877088Acetonitrile methylene chlorideHCID 178450552HCID 178450552, compound

Product 1

HCID 178517875HCID 178517875, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-5-[4-(2-tert-butoxy-ethoxy)-phenyl]-3-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-imidazolidine-2,4-dione (140 mg, 0.22 mmol) in 1:1 v/v dichloromethane/acetonitrile (2 mL) at 0° C. under an atmosphere of nitrogen was added sodium iodide (62 mg, 0.42 mmol) followed by chlorotrimethylsilane (78 μL, 0.61 mmol), the resulting solution was allowed to stir for 30 minutes. Additional sodium iodide (62 mg, 0.42 mmol) followed by chlorotrimethylsilane (78 μL, 0.61 mmol) was added and stirring continued for a further 45 minutes. The reaction was poured into ethyl acetate (30 mL) and washed with 10% aqueous sodium thiosulfate solution. The organic extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel gradient eluted with 60 to 80% v/v ethyl acetate/hexanes to give (R)-5-[4-(2-hydroxy-ethoxy)-phenyl]-3-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-imidazolidine-2,4-dione (83 mg, 65%).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for a further 45 minutes
  4. washwashed with 10% aqueous sodium thiosulfate solution
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by chromatography over silica gel gradient
  11. washeluted with 60 to 80% v/v ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d2c58e63de01467199cbc11933fd7e63
Source dataset
uspto-grants-2009_07
Patent number
US07557221B2

Reaction notes

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