Ethylenediamine → Glycyrrhetinic acid ethylenediamine

HRID 705059

Reaktionsgleichung

Reaktionsgleichung von HRID 705059
[CH3:1][C@@:2]12[CH2:24][CH2:23][C@:22]3([CH3:25])[C:8](=[CH:9][C:10]([C@H:12]4[C@@:21]3([CH3:26])[CH2:20][CH2:19][C@@H:18]3[C@:13]4([CH3:54])[CH2:14][CH2:15][C@H:16]([O:29][C@H:30]4[O:35][C@H:34]([C:36]([OH:38])=[O:37])[C@@H:33]([OH:39])[C@H:32]([OH:40])[C@H:31]4[O:41][C@@H:42]4[O:47][C@H:46]([C:48]([OH:50])=[O:49])[C@@H:45]([OH:51])[C@H:44]([OH:52])[C@H:43]4[OH:53])[C:17]3([CH3:28])[CH3:27])=[O:11])[C@@H:7]1[CH2:6][C@:5]([C:56]([OH:58])=[O:57])([CH3:55])[CH2:4][CH2:3]2.[CH2:59]([NH2:62])[CH2:60][NH2:61].C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:1][C@@:2]12[CH2:24][CH2:23][C@:22]3([CH3:25])[C:8](=[CH:9][C:10]([C@H:12]4[C@@:21]3([CH3:26])[CH2:20][CH2:19][C@@H:18]3[C@:13]4([CH3:54])[CH2:14][CH2:15][C@H:16]([O:29][C@H:30]4[O:35][C@H:34]([C:36]([OH:38])=[O:37])[C@@H:33]([OH:39])[C@H:32]([OH:40])[C@H:31]4[O:41][C@@H:42]4[O:47][C@H:46]([C:48]([OH:50])=[O:49])[C@@H:45]([OH:51])[C@H:44]([OH:52])[C@H:43]4[OH:53])[C:17]3([CH3:27])[CH3:28])=[O:11])[C@@H:7]1[CH2:6][C@:5]([C:56]([OH:58])=[O:57])([CH3:55])[CH2:4][CH2:3]2.[CH2:59]([NH2:62])[CH2:60][NH2:61]

Komponenten

5

Edukt 3

HCID 3301EthylenediamineHCID 10868DicyclohexylcarbodiimideHCID 14982Glycyrrhizin

Produkt 1

HCID 86634867Glycyrrhetinic acid ethylenediamineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To N,N′-dimethylformamide (10 mL) were added glycyrrhetinic acid (1.0 mmol, 0.474 g) and ethylenediamine (30.0 mmol, 1.8 g, 2.0 mL). To the obtained solution were added dicyclohexyl carbodiimide (1.2 mmol, 0.247 g) and 4-N,N′-dimethylaminopyridine (catalytic amount) at 0° C. The mixture was stirred for 0.5-1 hour at 0° C. and then refluxed for further 12-48 hours. The resultant solution was filtered. To the filtrate was dropwise added diethyl ether. The precipitate was recovered and dried under vacuum to give glycyrrhetinic acid-ethylenediamine (yield=92%).

Aufarbeitung

  1. temperaturerefluxed for further 12-48 hours
  2. filtrationThe resultant solution was filtered
  3. customThe precipitate was recovered
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-00b53f56056e4296abd143e2b0378110
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173852B2

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