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Cesium carbonate → 4-[4-((S)-1-{tert-butoxycarbonyl-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]amino}-ethyl)phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1019775
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HRID 1019775 반응식
[C:1]([O:5][C:6](=[O:31])[N:7]([C@H:22]([C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=1)[CH3:23])[CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][C:11]=1[Cl:21])([CH3:4])([CH3:3])[CH3:2].[C:32]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:35]([O:34][C:32]([N:39]1[CH2:44][CH2:43][N:42]([C:27]2[CH:28]=[CH:29][C:24]([C@@H:22]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:31])[CH2:8][CH2:9][C:10]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][C:11]=3[Cl:21])[CH3:23])=[CH:25][CH:26]=2)[CH2:41][CH2:40]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 67469177[(S)-1-(4-Bromo-phenyl)-ethyl]-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 674692684-[4-((S)-1-{tert-butoxycarbonyl-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]amino}-ethyl)phenyl]-piperazine-1-carboxylic acid tert-butyl ester수율 46%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of [(S)-1-(4-bromo-phenyl)-ethyl]-[2-(2-chloro-5-methoxy-4-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester (0.66 g, 1.17 mmol), N-Boc piperazine (0.44 g, 2.34 mmol), cesium carbonate (0.96 g, 2.92 mmol) and devphos (46.1 mg, 0.117 mmol) in 1,4-dioxane (5 mL) was degassed with argon. Pd2(dba)3 (0.054 g, 0.058 mmol) was added and the mixture heated to reflux for 3 hours under an argon atmosphere. The mixture was allowed to cool to room temperature, diluted with water (30 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using 20% EtOAc in hexane to give the title compound (0.33 g, 46%).

후처리

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3 hours under an argon atmosphere
  3. extractionextracted with EtOAc (3×30 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using 20% EtOAc in hexane

출처 및 근거

ORD 기록
ord-5e83f03b42d0425da666f8f706dcda73
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716287B2

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