Potassium Carbonate → HCID 19389039, Verbindung

HRID 1757858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757858
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Br[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:33]1([CH2:32][O:31][C:29](=[O:30])[CH2:28][NH:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 4457732HCID 4457732, Verbindung

Produkt 1

HCID 19389039HCID 19389039, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 1.08 g (3.0 mmol) of 3-(octadecyloxy)benzenamine, 0.52 ml (3.3mmol) of benzyl bromoacetate and 0.8 g (6.0 mmol) of potassium carbonate in40 ml of acetone was stirred at reflux under argon for 18 hours. The reaction mixture was filtered and the filtrate was concentrated at reducedpressure to an oil which was purified by chromatography on 150 g of silica gel using 20% ethyl acetate-hexane to give 1.1 g (72% yield, mp 55°-60°) of N-[3-(octadecyloxy) phenyl]glycine phenylmethyl ester.

Aufarbeitung

  1. temperatureat reflux under argon for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reducedpressure to an oil which
  4. customwas purified by chromatography on 150 g of silica gel using 20% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f274a006bb3c45528cca83f5c7901d0e
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446189

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