1-Propanamine, N,N-dimethyl-2,3-bis[(9Z)-9-octadecenyloxy]- → (2,3-Bis-octadec-9-enyloxypropyl)-(17-hydroxy-3,6,9,12,15-pentaoxoheptadecyl-oxycarbonylbutyl)-dimethylammonium bromide

HRID 1056465Notes

Reaction equation

HRID 1056465 reaction equation
[CH2:1]([O:19][CH:20]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:21][N:22]([CH3:24])[CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:45][CH2:46][CH2:47][C:48](=[O:75])[CH2:49][CH2:50][C:51](=[O:74])[CH2:52][CH2:53][C:54](=[O:73])[CH2:55][CH2:56][C:57](=[O:72])[CH2:58][CH2:59][C:60](=[O:71])[CH2:61][CH2:62][O:63][C:64](=[O:70])[CH2:65][CH2:66][CH2:67][CH2:68][Br:69]>CC(C)=O>[Br-:69].[CH2:1]([O:19][CH:20]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:21][N+:22]([CH2:68][CH2:67][CH2:66][CH2:65][C:64]([O:63][CH2:62][CH2:61][C:60](=[O:71])[CH2:59][CH2:58][C:57](=[O:72])[CH2:56][CH2:55][C:54](=[O:73])[CH2:53][CH2:52][C:51](=[O:74])[CH2:50][CH2:49][C:48](=[O:75])[CH2:47][CH2:46][OH:45])=[O:70])([CH3:24])[CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 538442591-Propanamine, N,N-dimethyl-2,3-bis[(9Z)-9-octadecenyloxy]-HCID 866435565-Bromopentanoic acid 17-hydroxy-3,6,9,12,15-pentaoxoheptadecyl ester

Product 1

HCID 86643554(2,3-Bis-octadec-9-enyloxypropyl)-(17-hydroxy-3,6,9,12,15-pentaoxoheptadecyl-oxycarbonylbutyl)-dimethylammonium bromideYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4 (395 mg, 0.64 mmol) and 8 (330 mg, 0.74 mmol) in acetone (5 ml) was stirred in a sealed-tube at RT for 24 h and than at 80° C. for another 24 h. After cooling, the solvent was evaporated in vacuo. Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane) gave ME52 as an orange oil (300 mg, 47%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated in vacuo
  3. customPurification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-dd03723186df40abae31207a31730556
Source dataset
uspto-grants-2016_07
Patent number
US09399016B2

Reaction notes

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