2-Bromoethanol → HCID 71475744, compound

HRID 1471449Notes

Reaction equation

HRID 1471449 reaction equation
[C:1]([O:16][CH2:17][CH2:18][N:19]([C:38](=[O:45])[CH2:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])[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:46][CH2:47][CH2:48][OH:49]>C(#N)C>[Br-:46].[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:45])[CH2:39][CH2:40][CH2:41][N+:42]([CH2:47][CH2:48][OH:49])([CH3:43])[CH3:44])(=[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

4

Reactant 2

HCID 108982-BromoethanolHCID 72550264HCID 72550264, compound

Product 1

HCID 71475744HCID 71475744, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

In a sealed system, ((4-(dimethylamino)butanoyl)azanediyl)bis(ethane-2,1-diyl) ditetradecanoate (300 mg, 0.469 mmol) was dissolved in ACN (5 mL) and 2-bromoethanol (500 uL) was added. The reaction vessel was flushed with inert gas and then sealed. Reaction was heated to 80° C. and stirred overnight, then concentrated. Purification by silica gel chromatography with a DCM/MeOH gradient yielded 4-(bis(2-(tetradecanoyloxy)ethyl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-4-oxobutan-1-aminium bromide (140 mg). LCMS ESI+: m/z 684.4 (M+H).

Workup

  1. customThe reaction vessel was flushed with inert gas
  2. customsealed
  3. customReaction
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography with a DCM/MeOH gradient

Sources & evidence

ORD record
ord-b982c77384fe4e4eb92be7163dba3d3d
Source dataset
uspto-grants-2015_04
Patent number
US09011903B2

Reaction notes

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