2-Bromoethanol → HCID 71475721, compound

HRID 1471444Notes

Reaction equation

[C:1]([O:16][CH2:17][CH2:18][CH2:19][N:20]([C:40](=[O:45])[CH2:41][N:42]([CH3:44])[CH3:43])[CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[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:1]([O:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:40](=[O:45])[CH2:41][N+:42]([CH2:47][CH2:48][OH:49])([CH3:43])[CH3:44])(=[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]

Participants

Conditions

Temperature: 80 °C

Procedure

In a sealed system, ((2-(dimethylamino)acetyl)azanediyl)bis(propane-3,1-diyl) ditetradecanoate (246 mg, 0.385 mmol) was dissolved in ACN (10 mL), and 2-bromoethanol (500 uL) was added. The reaction vessel was flushed with inert gas and then sealed. The mixture was heated to 80° C., stirred overnight, and then cooled and concentrated in vacuo. Purification by silica gel chromatography with a DCM/MeOH gradient yielded 99 mg 2-(bis(3-(tetradecanoyloxy)propyl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-2-oxoethanaminium bromide. QTOF MS ESI+: m/z 683.6 (M+H).

Workup

customThe reaction vessel was flushed with inert gas
customsealed
temperaturecooled
concentrationconcentrated in vacuo
customPurification by silica gel chromatography with a DCM/MeOH gradient

Sources & evidence

ORD record: ord-12f2153e53584c07b91c2e9f589b872d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09011903B2

Reaction notes

Loading…