Methanol → HCID 12970023, compound

HRID 278497Notes

Reaction equation

HRID 278497 reaction equation
C([O:8][C@H:9]([C@H:11]([N:21]1[CH:25]=[C:24]([C:26]([NH2:28])=[O:27])[N:23]=[CH:22]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[CH3:10])C1C=CC=CC=1.I[Si](C)(C)C.CO>C(Cl)(Cl)Cl>[OH:8][C@H:9]([C@H:11]([N:21]1[CH:25]=[C:24]([C:26]([NH2:28])=[O:27])[N:23]=[CH:22]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 69690422HCID 69690422, compound

Product 1

HCID 12970023HCID 12970023, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-[(2S,3R)-2-(benzyloxy)-5-(2-chlorophenyl)-3-pentyl]imidazole-4-carboxamide (obtained in Example 3(9))(40 mg) and iodotrimethylsilane (0.02 ml) in chloroform (1 ml) was stirred at room temperature for 2 hours. The mixture was poured into methanol and the whole was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with water, aqueous sodium bisulfite and sodium bicarbonate, successively, and dried. The residue left after evaporation of solvent was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (20:1) to give a white powder of 1-[(2S,3R)-2-hydroxy-5-(2-chlorophenyl)-3-pentyl]imidazole-4-carboxamide (6.1 mg).

Workup

  1. customthe whole was evaporated in vacuo
  2. washwashed with water, aqueous sodium bisulfite and sodium bicarbonate
  3. customsuccessively, and dried
  4. waitThe residue left
  5. customafter evaporation of solvent
  6. customwas purified by column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane and methanol (20:1)

Sources & evidence

ORD record
ord-abd3fcc06a7941dc97299e3eb69873f4
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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