2-Bromoethanol → 2-((2-(bis(2-(oleoyloxy)ethyl)amino)-2-oxoethyl)thio)-N-(2-hydroxyethyl)-N,N-dimethylethanaminium bromide

HRID 1471455Notes

Reaction equation

HRID 1471455 reaction equation
[C:1]([O:20][CH2:21][CH2:22][N:23]([C:46](=[O:54])[CH2:47][S:48][CH2:49][CH2:50][N:51]([CH3:53])[CH3:52])[CH2:24][CH2:25][O:26][C:27](=[O:45])[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])(=[O:19])[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].[Br:55][CH2:56][CH2:57][OH:58]>>[Br-:55].[C:1]([O:20][CH2:21][CH2:22][N:23]([CH2:24][CH2:25][O:26][C:27](=[O:45])[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])[C:46](=[O:54])[CH2:47][S:48][CH2:49][CH2:50][N+:51]([CH2:56][CH2:57][OH:58])([CH3:53])[CH3:52])(=[O:19])[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

3

Reactant 2

HCID 108982-BromoethanolHCID 72550488(Z)-((2-((2-(dimethylamino)ethyl)thio)acetyl)azanediyl)bis(ethane-2,1-diyl) dioleate

Product 1

HCID 866758882-((2-(bis(2-(oleoyloxy)ethyl)amino)-2-oxoethyl)thio)-N-(2-hydroxyethyl)-N,N-dimethylethanaminium bromide

Conditions

Temperature
75 °C

Procedure

In a sealed system, (Z)-((2-((2-(dimethylamino)ethyl)thio)acetyl)azanediyl)bis(ethane-2,1-diyl) dioleate (540 mg, 0.693 mmol) was combined with 2-bromoethanol (319 uL, 4.50) was added. The reaction vessel was flushed with inert gas and then sealed. Reaction was heated to 75° C. and allowed to stir overnight. Next day, cooled and concentrated in vacuo. Purification by silica gel chromatography with DCM/MeOH gradient yielded 2-((2-(bis(2-(oleoyloxy)ethyl)amino)-2-oxoethyl)thio)-N-(2-hydroxyethyl)-N,N-dimethylethanaminium bromide (324 mg).

Workup

  1. additionwas added
  2. customThe reaction vessel was flushed with inert gas
  3. customsealed
  4. customReaction
  5. temperatureNext day, cooled
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography with DCM/MeOH gradient

Sources & evidence

ORD record
ord-1feb45e0715645b3abbdbae7c9d78c03
Source dataset
uspto-grants-2015_04
Patent number
US09011903B2

Reaction notes

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