4-(4-Aminophenyl)-4-oxobutanoic acid → 3-[p-(1-Chlorocyclopropylcarbonylamino)-benzoyl]-propionic acid

HRID 647808

Reaktionsgleichung

Reaktionsgleichung von HRID 647808
[Cl:1][C:2]1([C:5](Cl)=[O:6])[CH2:4][CH2:3]1.[NH2:8][C:9]1[CH:21]=[CH:20][C:12]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[CH:11][CH:10]=1>O1CCCC1>[Cl:1][C:2]1([C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[CH:20][CH:21]=2)=[O:6])[CH2:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 2432904-(4-Aminophenyl)-4-oxobutanoic acidHCID 10942508Cyclopropanecarbonyl chloride, 1-chloro-

Produkt 1

HCID 204833713-[p-(1-Chlorocyclopropylcarbonylamino)-benzoyl]-propionic acidAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.9 g (28.1 millimoles) of 1-chlorocyclopropanecarboxylic acid chloride are added, with stirring, to 4.5 g (23.3 millimoles) of 3-(p-aminobenzoyl)-propionic acid in 100 ml of absolute tetrahydrofuran. The reaction mixture is then stirred for 20 hours at room temperature, followed by 7 hours under reflux. A small amount of solid is filtered off and discarded, and the filtrate is concentrated. The residue obtained is recrystallized from ethyl acetate, giving 3.4 g (49% of theory) of 3-[p-(1-chlorocyclopropylcarbonylamino)-benzoyl]-propionic acid as colorless crystals, of melting point 178°-179° C.

Aufarbeitung

  1. waitfollowed by 7 hours
  2. temperatureunder reflux
  3. filtrationA small amount of solid is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe residue obtained
  6. customis recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-74d38cc0253c41d886bfa8b64df79659
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410529

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