Benzoyl chloride → N-Benzoyl-L-asparagine

HRID 1586024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586024
O.[NH2:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][C:5](=[O:7])[NH2:6].C(=O)([O-])[O-].[K+].[K+].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:17]([NH:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][C:5](=[O:7])[NH2:6])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 170358L-Asparagine, monohydrate

Produkt 1

HCID 7062826N-Benzoyl-L-asparagineAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of 2 g (0.013 mol) of L-asparagine monohydrate and 2.02 g (0.014 mol) of potassium carbonate in 15 ml of water, 1.51 ml (0.013 mol) of benzoyl chloride was added dropwise, over a period of 15 min., at room temperature. The stirring was continued for 2 hour, then the mixture was extracted with 10 ml of ether and the aqueous phase was acidified to pH 2 with concentrated hydrochloric acid. The white precipitate was filtered off, washed with water and purified by crystallization from isopropyl alcohol to give 2.1 g (68% yield) of the title compound at 190-192° C.; NMR (DMSO-d6): 2.62 (m, 2H, CH2); 3.32 (broad s, 1H, OH); 4.72 (m, 1H, CH); 6.64-8.0(m. 7H, aromatic, NH2); 8.6 (d, 1H, NH).

Aufarbeitung

  1. extractionthe mixture was extracted with 10 ml of ether
  2. filtrationThe white precipitate was filtered off
  3. washwashed with water
  4. custompurified by crystallization from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-54fd43f91c8848378c8cee151d4757e0
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942504

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