Cesium carbonate → Tert-butyl 2-((4-(acetamido)phenyl)amino)-4-phenethylbenzoate

HRID 2191850

反応式

HRID 2191850 の反応式
[NH2:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].I[C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>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([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C.CC(O)(C)C>[C:37]([NH:36][C:33]1[CH:34]=[CH:35][C:30]([NH:1][C:2]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[CH:11][C:3]=2[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:31][CH:32]=1)(=[O:39])[CH3:38]

参加物

10

反応物 4

HCID 10796Cesium carbonate2 回HCID 12147N-(4-Iodophenyl)acetamide2 回HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl4 回HCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

生成物 1

HCID 68957261Tert-butyl 2-((4-(acetamido)phenyl)amino)-4-phenethylbenzoate

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒4 回HCID 9811564Bis(dibenzylideneacetone)palladium触媒4 回HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To 2-methyl-2-propanol 2.5 mL solution of tert-butyl 2-amino-4-phenethylbenzoate 0.12 g were added cesium carbonate 0.26 g, N-(4-iodophenyl)acetamide 0.16 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 10 mg, tris(dibenzylideneacetone)dipalladium(0) 4.0 mg and palladium acetate 2.0 mg at room temperature, and it was stirred at 80° C. for 4 hours. Tris(dibenzylideneacetone)dipalladium(0) 4.0 mg, palladium acetate 2.0 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 10 mg were added to it, and it was stirred at 80° C. for 12 hours. Cesium carbonate 0.26 g, N-(4-iodophenyl)acetamide 0.16 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 1 mg, tris(dibenzylideneacetone)dipalladium(0) 4.0 mg and palladium acetate 2.0 mg were added to it, and it was stirred at 80° C. for 5 hours and 30 minutes. 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 10 mg, tris(dibenzylideneacetone)dipalladium(0) 4.0 mg and palladium acetate 2.0 mg were added to it, and it was stirred at 80° C. for 12 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=1:1] to give tert-butyl 2-((4-(acetamido)phenyl)amino)-4-phenethylbenzoate.

後処理

  1. stirringwas stirred at 80° C. for 12 hours
  2. stirringwas stirred at 80° C. for 5 hours and 30 minutes
  3. stirringwas stirred at 80° C. for 12 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. washafter washing with saturated sodium chloride aqueous solution
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-dbfd94e967844e8c9bff4522f7161d7c
出典データセット
uspto-grants-2012_12
特許番号
US08327467B2

関連ノート

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