Ethylenediamine → Glycyrrhetinic acid ethylenediamine

HRID 705059

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

temperaturerefluxed for further 12-48 hours
filtrationThe resultant solution was filtered
customThe precipitate was recovered
customdried under vacuum

Sources & evidence

ORD record: ord-00b53f56056e4296abd143e2b0378110
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173852B2

Linked notes

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