Methanol → HCID 67014384, compound

HRID 1072056Notes

Reaction equation

HRID 1072056 reaction equation
C([O:8][C@H:9]([C@H:11]([N:22]1[CH:26]=[C:25]([C:27]([NH2:29])=[O:28])[N:24]=[CH:23]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH3:21])[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:22]1[CH:26]=[C:25]([C:27]([NH2:29])=[O:28])[N:24]=[CH:23]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH3:21])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 69677845HCID 69677845, compound

Product 1

HCID 67014384HCID 67014384, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-[(2S,3R)-2-(benzyloxy)-5-(2-(methylthio)phenyl)-3-pentyl]imidazole-4-carboxamide (133 mg) and iodotrimethylsilane (0.16 ml) in chloroform (5 ml) was stirred at room temperature for 2 hours. The mixture was poured into cold 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-(methylthio)phenyl)-3-pentyl]imidazole-4-carboxamide (2) (62 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-d82281317fd64a078ed201092a1c2af2
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

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