Oxalyl chloride → tert-butyl 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoate

HRID 1673502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673502
C(Cl)(=O)C(Cl)=O.[C:7]([O:10][C:11]1[CH:21]=[CH:20][C:14]([CH:15]=[CH:16][C:17]([OH:19])=O)=[CH:13][CH:12]=1)(=[O:9])[CH3:8].[NH2:22][C:23]1[CH:35]=[C:34]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[C:7]([O:10][C:11]1[CH:12]=[CH:13][C:14](/[CH:15]=[CH:16]/[C:17]([NH:22][C:23]2[CH:35]=[C:34]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:33]=[CH:32][C:24]=2[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[O:19])=[CH:20][CH:21]=1)(=[O:9])[CH3:8]

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 516892Sodium BicarbonateHCID 58508592Tert-butyl 2-amino-4-phenoxybenzoate

Produkt 1

HCID 67343538tert-butyl 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2.0 mL of methylene chloride, 3.9 μL of N,N-dimethylformamide and 0.094 mL of oxalyl chloride were added to 206 mg of 4-acetoxycinnamic acid at room temperature sequentially and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 86 mg of tert-butyl 2-amino-4-phenoxybenzoate, 3.0 mL of methylene chloride and 0.67 mL of triethylamine and stirred at room temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1] to obtain tert-butyl 2-((E)-3-(4-acetoxyphenyl)acrylamido)-4-phenoxybenzoate.

Aufarbeitung

  1. stirringstirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1]

Quellen und Nachweise

ORD-Eintrag
ord-aaee3455ea144cc4a55c052e19c09dd0
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999132B2

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