Hydroxyamine hydrochloride → (S)-1-[1-hydroxy-4-phenyl-2-butyl]-imidazole-4-carbohydroxamic acid

HRID 278493Notes

Reaction equation

HRID 278493 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].[Si]([O:14][CH2:15][C@@H:16]([N:25]1[CH:29]=[C:28]([C:30]([O:32]C)=O)[N:27]=[CH:26]1)[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(C(C)(C)C)(C)C>CO>[OH:14][CH2:15][C@@H:16]([N:25]1[CH:29]=[C:28]([C:30]([NH:5][OH:6])=[O:32])[N:27]=[CH:26]1)[CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 53683119methyl (S)-1-[1-(tert-butyldimethylsilyloxy)-4-phenyl-2-butyl]imidazole-4-carboxylate

Product 1

HCID 86757895(S)-1-[1-hydroxy-4-phenyl-2-butyl]-imidazole-4-carbohydroxamic acidYield 43.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A powder of NaOMe (417 mg, 7.72 mmol) was added to an ice cooled solution of hydroxylamine hydrochloride (536 mg, 7.72 mmol) in methanol (5 ml). After 30 minutes, methyl (S)-1-[1-(tert-butyldimethylsilyloxy)-4-phenyl-2-butyl]imidazole-4-carboxylate (obtained in Example 6)(389 mg, 1.0 mmol) in methanol (2 ml) was added to the mixture and the resulting mixture was stirred at reflux for 3 day. After cooling, the insoluble material was removed and then the filtrate was evaporated. The residue was diluted with water and the solution was acidified to pH 4 with 1N HClaq. The resulting mixture was washed with CHCl3. The aqueous layer was purified by HP-20 (40 cc) column chromatography eluting with water/2-propanol (9:1) and lyophilized to give (S)-1-[1-hydroxy-4-phenyl-2-butyl]-imidazole-4-carbohydroxamic acid (92.5 mg, 43.5%) as an amorphous solid.

Workup

  1. temperatureat reflux for 3 day
  2. temperatureAfter cooling
  3. customthe insoluble material was removed
  4. customthe filtrate was evaporated
  5. additionThe residue was diluted with water
  6. washThe resulting mixture was washed with CHCl3
  7. customThe aqueous layer was purified by HP-20 (40 cc) column chromatography
  8. washeluting with water/2-propanol (9:1)

Sources & evidence

ORD record
ord-a1a90e369a2c44359e3bb8c9a7431da1
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

Loading…