Ethyl Acetate → [4-(2-Amino-4-benzoylaminophenoxy)phenyl]carbamic acid tert-butyl ester

HRID 605266ノート

反応式

HRID 605266 の反応式
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][C:16]=2[N+:30]([O-])=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1.O.[Fe]>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:29])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:17][C:16]=2[NH2:30])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 67040356[4-(4-Benzoylamino-2-nitrophenoxy)-phenyl]carbamic acid tert-butyl ester

生成物 1

HCID 67040690[4-(2-Amino-4-benzoylaminophenoxy)phenyl]carbamic acid tert-butyl ester収率 95.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The product from Example 252a (1.50 g, 3.3 mmol), Fe powder (0.78 g, 13.4 mmol) and NH4Cl (0.71 g, 13.4 mmol) in a mixture of THF (7.5 mL) and H2O (3 mL) was gradually heated to reflux and refluxed for 19 hours. The reaction mixture was portioned between EtOAc and 10% NaHCO3 and then filtered (through celite). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound which was purified by column chromatography on silica gel eluting with 1:1 n-hexane/EtOAc to give the title compound as a yellow foam (1.32 g, 94%).

後処理

  1. temperaturewas gradually heated
  2. temperatureto reflux
  3. temperaturerefluxed for 19 hours
  4. filtrationfiltered (through celite)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customgiving the crude title compound which
  10. customwas purified by column chromatography on silica gel eluting with 1:1 n-hexane/EtOAc

出典と根拠

ORDレコード
ord-3426851cbbe84134a877d7cec839906d
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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