Benzene → 3-(N-Tridecylcarbamoyloxy)propyl 2-trimethylammonioethyl phosphate
Reaction equation
[CH2:1]([NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:22]([OH:37])(=O)[CH2:23]CCCCCCCCCCCC.[P:38](Cl)(Cl)(=[O:43])[O:39]CCBr.[N:46]1[CH:51]=CC=C[CH:47]=1.[CH:52]1C=CC=CC=1>>[P:38]([O-:39])([O:37][CH2:22][CH2:23][N+:46]([CH3:51])([CH3:52])[CH3:47])([O:21][CH2:20][CH2:19][CH2:18][O:17][C:15](=[O:16])[NH:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:43]Participants
6
Procedure
In 23 ml of benzene are dissolved 4.0 g (13.27 mM) of 3-(N-tridecylcarbamoyloxy)propanol prepared from 9.12 g of myristic acid as in Example 18 and 4.82 g (19.90 mM) of 2-bromoethyl phosphorodichloridate. To the solution is added dropwise 1.57 g (19.90 mM) of pyridine, and the mixture is stirred at room temperature. As in Example 20, the reaction mixture is hydrolyzed, converted to a quaternary ammonium compound, dehalogenated and purified by silica gel chromatography to give the contemplated compound as colorless solid. Yield 3.5 g.
Workup
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-5ec486fdce0643258db2833bb552bd6e
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04565865
Reaction notes
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