Acetic Acid → 3-(tert-Butyloxycarbonyl)-7-(5-methyl-oxazol-2-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 33218

反応式

HRID 33218 の反応式
[CH2:1]([NH:4][C:5]([C:7]1[CH:17]=[CH:16][C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:6])[C:2]#[CH:3].[C:18]([OH:21])(=[O:20])C>C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[C:7]([O:21][C:18]([N:13]1[CH2:12][CH2:11][C:10]2[CH:16]=[CH:17][C:7]([C:5]3[O:6][C:2]([CH3:3])=[CH:1][N:4]=3)=[CH:8][C:9]=2[CH2:15][CH2:14]1)=[O:20])([CH3:17])([CH3:8])[CH3:5]

参加物

4

反応物 2

HCID 176Acetic AcidHCID 865941712,3,4,5-tetrahydro-1H-3-benzazepine-7-carboxylic acid prop-2-ynyl amide

生成物 1

HCID 236311743-(tert-Butyloxycarbonyl)-7-(5-methyl-oxazol-2-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

試薬・触媒・溶媒 1

HCID 15337Mercuric acetate触媒

実験手順

A mixture of 2,3,4,5-tetrahydro-1H-3-benzazepine-7-carboxylic acid prop-2-ynyl amide (3.8 g) and mercury (II) acetate (350 mg) in glacial acetic acid was heated under reflux for 1.5 h. After cooling, the solvent was removed in vacuo and the residue partitioned between EtOAc (200 ml) and saturated NaHCO3 solution (100 ml). The aqueous layer was re-extracted with EtOAc and the combined organic layers dried and evaporated in vacuo. The residue was purified using silica gel chromatography (gradient elution, hexane/EtOAc) to give the title compound (2.35 g) as a colourless oil.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue partitioned between EtOAc (200 ml) and saturated NaHCO3 solution (100 ml)
  6. extractionThe aqueous layer was re-extracted with EtOAc
  7. customthe combined organic layers dried
  8. customevaporated in vacuo
  9. customThe residue was purified
  10. washsilica gel chromatography (gradient elution, hexane/EtOAc)

出典と根拠

ORDレコード
ord-ddafd4156ff14d62adea9bbedf94f845
出典データセット
uspto-grants-2008_09
特許番号
US07429579B2

関連ノート

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