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Citric Acid → HCID 68963145, 화합물

HRID 2191811
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HRID 2191811 반응식
[NH2:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=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:33]1[CH:38]=[CH:37][C:36]2[O:39][CH2:40][O:41][C:35]=2[CH:34]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)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([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[O:39]1[C:36]2[CH:37]=[CH:38][C:33]([NH:1][C:2]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:34][C:35]=2[O:41][CH2:40]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 1386201-Iodo-3,4-methylenedioxybenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl2회HCID 68959354HCID 68959354, 화합물

생성물 1

HCID 68963145HCID 68963145, 화합물

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매2회HCID 9811564Bis(dibenzylideneacetone)palladium촉매2회HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-(4-(methanesulfonamido)phenyl)benzoate 0.12 g and cesium carbonate 0.27 g were added 1-iodo-3,4-methylenedioxybenzene 0.16 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.9 mg, tris(dibenzylideneacetone)dipalladium(0) 3.0 mg and palladium acetate 1.5 mg at room temperature, and it was stirred at 110° C. for 24 hours. 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.9 mg, tris(dibenzylideneacetone)dipalladium(0) 3.0 mg and palladium acetate 1.5 mg were added to it, and it was stirred at 110° C. for 21 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it, and insoluble matter was filtrated. 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=2:1] to give tert-butyl 2-((benzo-1,3-dioxol-5-yl)amino)-4-(4-(methanesulfonamido)phenyl)benzoate.

후처리

  1. stirringwas stirred at 110° C. for 21 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationwas filtrated
  4. customThe organic layer was separated
  5. washafter washing with saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-a4c3db0ab0d6479fa876681f7fc1974f
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08327467B2

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