Hydrochloric Acid → tert-butyl 4-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoate

HRID 1673537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673537
C(Cl)(=O)C(Cl)=O.[N:7]1([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8]1.[NH2:21][C:22]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:32]=[CH:31][C:23]=1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].Cl>C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[C:35]1([C:33]2[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[C:22]([NH:21][C:16](=[O:18])[C:15]3[CH:14]=[CH:13][C:12]([N:7]4[CH:8]=[CH:9][CH:10]=[CH:11]4)=[CH:20][CH:19]=3)[CH:34]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 27372564-(1H-Pyrrol-1-yl)benzoic acidHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Produkt 1

HCID 67344178tert-butyl 4-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.015 mL of N,N-dimethylformamide was added to a mixed solution of 2.0 mL of methylene chloride and 0.024 mL of oxalyl chloride containing 47 mg of 4-(1H-pyrrol-1-yl)benzoic acid and stirred at room temperature for 30 minutes. 67 mg of tert-butyl 2-amino-4-phenylbenzoate and 0.090 mL of triethylamine were added to the reaction mixture at room temperature sequentially and stirred at the same temperature for 30 minutes. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform] to obtain 64 mg of tert-butyl 4-phenyl-2-(4-(1H-pyrrol-1-yl)benzamido)benzoate as white solid.

Aufarbeitung

  1. stirringstirred at the same temperature for 30 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium chloride aqueous solution
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform]

Quellen und Nachweise

ORD-Eintrag
ord-9672b81898db434793a1112ed4716ce0
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999132B2

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