Trimethylsilyl iodide → 1-[(2S,3R)-5-(3,4-dichlorophenoxy)-2-hydroxy-3-pentyl]imidazole-4-carboxamide

HRID 1829804Notes

Reaction equation

HRID 1829804 reaction equation
C([O:8][C@H:9]([C@H:11]([N:23]1[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]1)[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[CH3:10])C1C=CC=CC=1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[Cl:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[Cl:21])[O:14][CH2:13][CH2:12][C@@H:11]([N:23]1[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]1)[C@@H:9]([OH:8])[CH3:10]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 101609361-[(2S,3R)-2-benzyloxy-5-(3,4-dichlorophenoxy)-3-pentyl]imidazole-4-carboxamide

Product 1

HCID 101330051-[(2S,3R)-5-(3,4-dichlorophenoxy)-2-hydroxy-3-pentyl]imidazole-4-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice cooled solution of 1-[(2S,3R)-2-benzyloxy-5-(3,4-dichlorophenyloxy)-3-pentyl]imidazole-4-carboxamide (59.5 mg, 0.133 mmol) in chloroform (5 ml) was added trimethylsilyl iodide (34.5 mg, 0.173 mmol). After 3 minutes, the ice bath was removed, and then stirred at room temperature overnight. The reaction was quenched by addition of methanol. This mixture was extracted with ethyl acetate, and the extracts were washed with brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (2.5 g) chromatography eluting with chloroform/methanol (50:1 to 10:1) to give 1-[(2S,3R)-5-(3,4-dichlorophenoxy)-2-hydroxy-3-pentyl]imidazole-4-carboxamide (4) (40.4 mg, 85.0%) as a white amorphous solid.

Workup

  1. customthe ice bath was removed
  2. customThe reaction was quenched by addition of methanol
  3. extractionThis mixture was extracted with ethyl acetate
  4. washthe extracts were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel (2.5 g) chromatography
  8. washeluting with chloroform/methanol (50:1 to 10:1)

Sources & evidence

ORD record
ord-e03ad119fd0344f3a6bcf52aba66a696
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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