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

HRID 1022663

反応式

HRID 1022663 の反応式
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

参加物

7

反応物 4

HCID 176Acetic AcidHCID 14742,2'-BipyridineHCID 4311764Sodium borohydrideHCID 86663863HCID 86663863、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 24610Cobalt dibromide触媒HCID 702Ethanol溶媒2 回

反応条件

温度
2.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1253be1d357643009d53a3f1f5bbcd89
出典データセット
uspto-grants-2014_05
特許番号
US08722662B2

関連ノート

読み込み中…