2-Bromoethanol → HCID 71475746, compound

HRID 1471453Notes

Reaction equation

HRID 1471453 reaction equation
[C:1]([O:16][CH2:17][CH2:18][N:19]([C:38](=[O:46])[CH2:39][S:40][CH2:41][CH2:42][N:43]([CH3:45])[CH3:44])[CH2:20][CH2:21][O:22][C:23](=[O:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Br:47][CH2:48][CH2:49][OH:50]>>[Br-:47].[C:23]([O:22][CH2:21][CH2:20][N:19]([CH2:18][CH2:17][O:16][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:38](=[O:46])[CH2:39][S:40][CH2:41][CH2:42][N+:43]([CH2:48][CH2:49][OH:50])([CH3:44])[CH3:45])(=[O:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

3

Reactant 2

HCID 108982-BromoethanolHCID 725504871415840-66-2

Product 1

HCID 71475746HCID 71475746, compoundYield 66.6%

Conditions

Temperature
75 °C

Procedure

In a sealed system, ((2-((2-(dimethylamino)ethyl)thio)acetyl)azanediyl)bis(ethane-2,1-diyl) ditetradecanoate (1.00 g, 1.49 mmol) was combined with 2-bromoethanol (687 uL, 9.69 mmol) was added. The reaction vessel was flushed with inert gas and then sealed. Reaction was heated to 75° C. and allowed to stir overnight, then cooled, and concentrated in vacuo. Purification by silica gel chromatography with DCM/MeOH gradient yielded 2-((2-(bis(2-(tetradecanoyloxy)ethyl)amino)-2-oxoethyl)thio)-N-(2-hydroxyethyl)-N,N-dimethylethanaminium bromide (HES104) (790 mg). LCMS ESI+: m/z 715.7 (M+H).

Workup

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

Sources & evidence

ORD record
ord-4fdcb4e0a9ff437aac2f5b1119f00c00
Source dataset
uspto-grants-2015_04
Patent number
US09011903B2

Reaction notes

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