Triethylamine → Tert-butyl 4-(benzo[1,3]dioxol-5-yl)-2-(4-fluorobenzamido)benzoate

HRID 1673437

Reaktionsgleichung

Reaktionsgleichung von HRID 1673437
C(N(CC)CC)C.[F:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[NH2:18][C:19]1[CH:31]=[C:30]([C:32]2[CH:40]=[CH:39][C:35]3[O:36][CH2:37][O:38][C:34]=3[CH:33]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])O.[Na+]>C(Cl)Cl>[O:36]1[C:35]2[CH:39]=[CH:40][C:32]([C:30]3[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[C:19]([NH:18][C:13](=[O:14])[C:12]4[CH:16]=[CH:17][C:9]([F:8])=[CH:10][CH:11]=4)[CH:31]=3)=[CH:33][C:34]=2[O:38][CH2:37]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 67342168Tert-butyl 2-amino-4-(benzo[1,3]dioxol-5-yl)benzoate

Produkt 1

HCID 67344518Tert-butyl 4-(benzo[1,3]dioxol-5-yl)-2-(4-fluorobenzamido)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.054 mL of triethylamine and 0.034 mL of 4-fluorobenzoyl chloride were added to 3.5 mL of methylene chloride solution containing 60 mg of tert-butyl 2-amino-4-(benzo[1,3]dioxol-5-yl)benzoate at room temperature sequentially and stirred at the same temperature for 5 hours. 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 4-(benzo[1,3]dioxol-5-yl)-2-(4-fluorobenzamido)benzoate.

Aufarbeitung

  1. customthe organic layer was separated
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008

Quellen und Nachweise

ORD-Eintrag
ord-d5087cd630064ce29b876388cc079ca8
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999132B2

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