Triethylamine → 2-(Benzoyloxy)-3-(octadecyloxy)propyl 10-trimethylammoniodecyl phosphate

HRID 868439Notes

Reaction equation

HRID 868439 reaction equation
[C:1]([O:9][CH:10]([CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:11][OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[P:40](Cl)(Cl)(Cl)=[O:41].S([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][N+:66]([CH3:69])([CH3:68])[CH3:67])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[OH:71].[Na+]>C(O)C.N1C=CC=CC=1>[P:40]([O-:41])([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][N+:66]([CH3:67])([CH3:68])[CH3:69])([O:12][CH2:11][CH:10]([O:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:71]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 138719511-Octadecyl-2-benzoylglycerolHCID 13171573010-Trimethylammoniodecylalcohol monotosylate

Product 1

HCID 141280722-(Benzoyloxy)-3-(octadecyloxy)propyl 10-trimethylammoniodecyl phosphateYield 43.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1049PyridineSolvent

Procedure

2.24 g (5.0 mmole) of 2-benzoyloxy-3-octadecyloxypropanol was dissolved in 20 ml of ethanol-free chloroform and 2.63 g (26.0 mmole) of dry triethylamine was added thereto under ice-cooling. Then, 0.81 g (5.3 mmole) of phosphorus oxychloride in 40 ml of ethanol-free chloroform was further added, and the resulting mixture was stirred under ice-cooling for 30 minutes and at room temperature for 1 hour. This reaction mixture was again cooled on ice, and 2.80 g (7.5 mmole) of 10-trimethylammoniodecylalcohol monotosylate in 80 ml of dry pyridine was added thereto. The reaction mixture was stirred under ice-cooling for 30 minutes and at room temperature for 18 hours. To the reaction mixture was added an aqueous solution containing 3.5 g sodium hydrogencarbonate and the resulting mixture was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on Amberlite resin (IR-120: IRA-410=1:2; eluent: 95% THF) and then further by column chromatography on silica gel (Merck, Art 7734; eluent: chloroform-methanol-water=65:25:4) to give 1.57 g (yield: 43.4%) of the desired product.

Workup

  1. temperatureunder ice-cooling
  2. additionwas added
  3. stirringThe reaction mixture was stirred under ice-
  4. temperaturecooling for 30 minutes and at room temperature for 18 hours
  5. additionTo the reaction mixture was added an aqueous solution
  6. concentrationthe resulting mixture was concentrated to dryness under reduced pressure
  7. customThe residue was purified by column chromatography on Amberlite resin (IR-120: IRA-410=1:2; eluent: 95% THF)

Sources & evidence

ORD record
ord-a3f13bffe0524fab860affd062d06761
Source dataset
uspto-grants-1988_10
Patent number
US04778912

Reaction notes

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