2-(Benzyloxy)-3-(octadecyloxy)propyl 8-trimethylammoniooctyl phosphate → 2-(Hydroxy)-3-(octadecyloxy)propyl 8-trimethylammoniooctyl phosphate

HRID 868446Notes

Reaction equation

HRID 868446 reaction equation
[P:1]([O-:47])([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N+:43]([CH3:46])([CH3:45])[CH3:44])([O:3][CH2:4][CH:5]([O:26]CC1C=CC=CC=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2].[H][H]>C(O)(=O)C.[Pd]>[P:1]([O-:47])([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N+:43]([CH3:46])([CH3:45])[CH3:44])([O:3][CH2:4][CH:5]([OH:26])[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2]

Participants

5

Reactant 2

HCID 212884102-(Benzyloxy)-3-(octadecyloxy)propyl 8-trimethylammoniooctyl phosphateHCID 178418361HCID 178418361, compound

Product 1

HCID 212883902-(Hydroxy)-3-(octadecyloxy)propyl 8-trimethylammoniooctyl phosphateYield 28.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

290 mg (0.43 mmole) of 2-(benzyloxy)-3-(octadecyloxy)propyl 8-trimethylammoniooctyl phosphate was dissolved in 30 ml of 70% acetic acid, and 0.2 g of 10% Pd-C as a catalyst was added to the mixture. The mixture was stirred at room temperature for 4 hours in a hydrogen atmosphere and filtrated. The filtrate was concentrated to dryness under reduced pressure and the residue was purified by silica gel (3 g, Merck & Co., Art. 7734; eluent: chloroform:methanol:water=65:25:4) column chromatography to give 72 mg (yield: 28.7%) of the above-mentioned compound.

Workup

  1. filtrationfiltrated
  2. concentrationThe filtrate was concentrated to dryness under reduced pressure
  3. customthe residue was purified by silica gel (3 g, Merck & Co., Art. 7734; eluent: chloroform:methanol:water=65:25:4) column chromatography

Sources & evidence

ORD record
ord-1b3dd38afffd409bbfe4b1b7f869eff6
Source dataset
uspto-grants-1988_10
Patent number
US04778912

Reaction notes

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