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

HRID 278493ノート

反応式

HRID 278493 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a1a90e369a2c44359e3bb8c9a7431da1
出典データセット
uspto-grants-2002_03
特許番号
US06359145B1

反応ノート

読み込み中…