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

HRID 278493노트

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HRID 278493 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a1a90e369a2c44359e3bb8c9a7431da1
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359145B1

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