3-(Dimethylamino)-1,2-propanediol → (2,3-Bis-octadec-9-enyloxypropyl)-(8-hydroxy-3,6-dioxooctyloxycarbonylbutyl)-dimethylammonium bromide

HRID 1056463Notes

Reaction equation

HRID 1056463 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].S(OCCCCCCCCC=CCCCCCCCC)(=O)(=O)C.CN(C)CC(O)CO.[OH:76][CH2:77][CH2:78][C:79](=[O:94])[CH2:80][CH2:81][C:82](=[O:93])[CH2:83][CH2:84][O:85][C:86](=[O:92])[CH2:87][CH2:88][CH2:89][CH2:90][Br:91]>CC(C)=O>[Br-:91].[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]([CH2:90][CH2:89][CH2:88][CH2:87][C:86]([O:85][CH2:84][CH2:83][C:82](=[O:93])[CH2:81][CH2:80][C:79](=[O:94])[CH2:78][CH2:77][OH:76])=[O:92])([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

6

Reactant 4

HCID 790783-(Dimethylamino)-1,2-propanediolHCID 1188619-Octadecen-1-ol, methanesulfonate, (9Z)-HCID 538442591-Propanamine, N,N-dimethyl-2,3-bis[(9Z)-9-octadecenyloxy]-HCID 866435505-Bromopentanoic acid 8-hydroxy-3,6-dioxooctyl ester

Product 1

HCID 86643548(2,3-Bis-octadec-9-enyloxypropyl)-(8-hydroxy-3,6-dioxooctyloxycarbonylbutyl)-dimethylammonium bromideYield 27%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (2,3-bis-octadec-9-enyloxypropyl)-dimethylamine 4 (378 mg, 0.61 mmol) (synthesised from octadec-9-enyl mesylate and 3-dimethylamino-1,2-propanediol as described previously by Hurley et al., J. Org. Chem., 2004, 69, 980-984) and 3 (335 mg, 1.07 mmol) in acetone (5 ml) was stirred in a sealed-tube at 80° C. for 48 h. After cooling, the solvent was evaporated in vacuo. Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane) gave ME42 as an orange oil (140 mg, 27%).

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-5f67299e3cc9467f89fa2a7044a78088
Source dataset
uspto-grants-2016_07
Patent number
US09399016B2

Reaction notes

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