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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
ノート
印刷プレビュー

反応式

HRID 1019775 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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 ester収率 46%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5e83f03b42d0425da666f8f706dcda73
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08716287B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート