Acetic Acid → tert-butyl (6SR,7SR)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022663

반응식

HRID 1022663 반응식
N1C=CC=CC=1C1C=CC=CN=1.[BH4-].[Na+].[N:15]([CH:18]1[CH:24]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[O:23][CH2:22][CH2:21][N:20]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:19]1)=[N+]=[N-].C(O)(=O)C>C(O)C.[Co](Br)Br>[NH2:15][CH:18]1[CH:24]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[O:23][CH2:22][CH2:21][N:20]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:19]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 14742,2'-BipyridineHCID 4311764Sodium borohydrideHCID 86663863HCID 86663863, 화합물

생성물 1

HCID 66975299tert-butyl (6SR,7SR)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate수율 75.8%

시약·촉매·용매 2

HCID 24610Cobalt dibromide촉매HCID 702Ethanol용매2회

반응 조건

온도
2.5 °C

실험 절차

To a solution of cobalt bromide (15 mg) in ethanol (5 mL) was added 2,2′-bipyridyl (33 mg), sodium tetrahydroborate (53 mg) was added, and the mixture was stirred at 0-5° C. for 5 min. To the reaction mixture was added a solution of tert-butyl (6SR,7SR)-6-azido-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (270 mg) in ethanol (5 mL), and the mixture was stirred at 0-5° C. for 30 min. Acetic acid was added to the reaction mixture, and the mixture was stirred at room temperature for 5 min. The solvent was evaporated under reduced pressure. The residue was neutralized with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (191 mg).

후처리

  1. additionwas added
  2. stirringthe mixture was stirred at 0-5° C. for 30 min
  3. stirringthe mixture was stirred at room temperature for 5 min
  4. customThe solvent was evaporated under reduced pressure
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1253be1d357643009d53a3f1f5bbcd89
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722662B2

연결된 노트

불러오는 중…