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

HRID 868440Notes

Reaction equation

HRID 868440 reaction equation
[CH2:1]([O:8][CH:9]([CH2:12][O:13][CH2:14][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][CH3:31])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[P:39](Cl)(Cl)(Cl)=[O:40].S([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][N+:65]([CH3:68])([CH3:67])[CH3:66])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[OH:70].[Na+]>C(O)C.N1C=CC=CC=1>[P:39]([O-:40])([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][N+:65]([CH3:66])([CH3:67])[CH3:68])([O:11][CH2:10][CH:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:12][O:13][CH2:14][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][CH3:31])=[O:70]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 131165252-(Benzyloxy)-3-(octadecyloxy)propan-1-OLHCID 131715730HCID 131715730, compound

Product 1

HCID 142809452-(Benzyloxy)-3-(octadecyloxy)propyl 10-trimethylammoniodecyl phosphateYield 34.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1049PyridineSolvent

Procedure

2.34 g (5.4 mmole) of 2-benzyloxy-3-octadecyloxypropanol was dissolved in 20 ml of ethanol-free chloroform and 2.83 g (28.0 mmole) of dry triethylamine was added thereto under ice-cooling. Then, 0.87 g (5.7 mmole) of phosphorus oxychloride in 40 ml of ethanol-free chloroform was further added. The reaction mixture was stirred under ice-cooling for 30 minutes and at room temperature for 1 hour. This reaction mixture was again cooled on an ice bath and 3.00 g (8.07 mmole) of 10-trimethylammoniodecylalcohol monotosylate in 80 ml of dry pyridine was added to the mixture. The resulting mixture was stirred under ice-cooling for 30 minutes and at room temperature for 16 hours. An aqueous solution containing 3.8 g of sodium hydrogencarbonate was added to the reaction mixture and the reaction mixture was concentrated to dryness under reduced pressure. The residue was purified by Amberlite resin column chromatography (IR-120: IRA-410=1:2; eluent: 95% THF) and by silica gel column chromatography (Merck & Co., Art. 7734, eluent: chloroform-methanol:water=65:25:4) to give 1.32 g (yield: 34.3%) of the desired product.

Workup

  1. temperatureunder ice-cooling
  2. temperatureThis reaction mixture was again cooled on an ice bath
  3. stirringThe resulting mixture was stirred under ice-
  4. temperaturecooling for 30 minutes and at room temperature for 16 hours
  5. additionwas added to the reaction mixture
  6. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  7. customThe residue was purified by Amberlite resin column chromatography (IR-120: IRA-410=1:2; eluent: 95% THF) and by silica gel column chromatography (Merck & Co., Art. 7734, eluent: chloroform-methanol:water=65:25:4)

Sources & evidence

ORD record
ord-817cc3adf84f44e9a17b0dceb9d2c4fc
Source dataset
uspto-grants-1988_10
Patent number
US04778912

Reaction notes

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