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

HRID 605266노트

반응식

HRID 605266 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-3426851cbbe84134a877d7cec839906d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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