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

HRID 33218

반응식

HRID 33218 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 15337Mercuric acetate촉매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ddafd4156ff14d62adea9bbedf94f845
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429579B2

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