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

HRID 2191850

반응식

HRID 2191850 반응식
[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]

참가 물질

10

반응물 4

HCID 10796Cesium carbonate2회HCID 12147N-(4-Iodophenyl)acetamide2회HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl4회HCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

생성물 1

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

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매4회HCID 9811564Bis(dibenzylideneacetone)palladium촉매4회HCID 962Water용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dbfd94e967844e8c9bff4522f7161d7c
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08327467B2

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