Dimethylformamide → N-tert-butyl-2-(3-azido-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl) ethanoic acid amide

HRID 53129

反応式

HRID 53129 の反応式
[C:1]([NH:5][C:6](=[O:27])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10](Br)[C:9]1=[O:26])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.[N-:33]=[N+:34]=[N-:35].[Na+].[N-]=[N+]=[N-]>O>[C:1]([NH:5][C:6](=[O:27])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10]([N:33]=[N+:34]=[N-:35])[C:9]1=[O:26])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 33558AzideHCID 15203361N-tert-butyl 2-(3-bromo-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl) ethanoic acid amide

生成物 1

HCID 15203363N-tert-butyl-2-(3-azido-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl) ethanoic acid amide収率 80.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a 125 ml round-bottomed flask equipped with a nitrogen inlet were added 8.2 grams (18.5 mmol) N-tert-butyl 2-(3-bromo-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-1-yl) ethanoic acid amide and 40 ml dimethylformamide. After dissolution, a solution of 1.44 grams (22.2 mmol) sodium azide in 2 mL water (with two additional 0.75 ml portions of water) was added, and the solution heated at 80°-85° C. for 4 hours 20 minutes (at this point, tlc and NMR of an aliquot indicated a 75/15/10 ratio of desired azide/isomeric azide/starting material). The reaction was cooled, poured into water, and extracted twice into ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel using 3:1 hexane/ethyl acetate to give 5.80 grams (77%) of a foam which solidified.

後処理

  1. customTo a 125 ml round-bottomed flask equipped with a nitrogen inlet
  2. dissolutionAfter dissolution
  3. temperaturethe solution heated at 80°-85° C. for 4 hours 20 minutes (at this point, tlc and NMR of an aliquot
  4. temperatureThe reaction was cooled
  5. extractionextracted twice into ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel using 3:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-acf1ed8415ef4064844a16e2644ce761
出典データセット
uspto-grants-1997_04
特許番号
US05618811

関連ノート

読み込み中…