Acetic Acid → 5-Amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 496408ノート

反応式

HRID 496408 の反応式
[N+:1]([C:4]1[C:13]([O:14][C@@H:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][C:9]2=[O:28])([O-])=O.CO.C(O)(=O)C.C([O-])(O)=O.[Na+]>[Fe].CO.C(Cl)Cl.CCOC(C)=O.O>[NH2:1][C:4]1[C:13]([O:14][C@@H:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][C:9]2=[O:28]

参加物

9

反応物 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 600298755-nitro-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

生成物 1

HCID 600298675-Amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one収率 76%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

A mixture of 5-nitro-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (2.05 g, 5.43 mmol), MeOH (135 mL), H2O (30 mL) and glacial acetic acid (3.1 mL, 54 mmol) was treated at reflux with iron powder (3.01 g, 54 mmol). The reaction was monitored by mass spectrometry and was complete in 5 h. The volume of solvent was reduced under reduced pressure. EtOAc and dilute aqueous NaHCO3 were added. A brownish-green emulsion formed which was filtered through Celite. The mixture was extracted with EtOAc. The combined organic layer was washed with dilute aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated under reduced pressure to give a brown solid. Purification by chromatography (EtOAc then 6% MeOH/CH2Cl2) gave the product as a tan solid (1.43 g, 4.12 mmol, 76%). The structure was confirmed by NMR and mass spectrometry. MS m/z 348 (M++H).

後処理

  1. additionwas treated
  2. customA brownish-green emulsion formed which
  3. filtrationwas filtered through Celite
  4. extractionThe mixture was extracted with EtOAc
  5. washThe combined organic layer was washed with dilute aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give a brown solid
  9. customPurification by chromatography (EtOAc

出典と根拠

ORDレコード
ord-c76182f548b94a59ac1c9392ce917451
出典データセット
uspto-grants-2005_09
特許番号
US06943183B2

反応ノート

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