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

HRID 868441Notes

Reaction equation

HRID 868441 reaction equation
[P:1]([O-:49])([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][N+:45]([CH3:48])([CH3:47])[CH3:46])([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]>C(O)C.C(O)(=O)C.[Pd]>[P:1]([O-:49])([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][N+:45]([CH3:48])([CH3:47])[CH3:46])([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 1

HCID 142809452-(Benzyloxy)-3-(octadecyloxy)propyl 10-trimethylammoniodecyl phosphate

Product 1

HCID 141280742-(Hydroxy)-3-(octadecyloxy)propyl 10-trimethylammoniodecyl phosphateYield 88.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

1.31 g (1.8 mmole) of the compound of Example 4 was dissolved in a mixture of 100 ml of ethanol and 50 ml of 70% acetic acid. Then, 0.6 g of 10% Pd-C was added thereto and catalytic reduction was carried out at room temperature. 19 hours later, the reaction mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was solidified by acetone to give 994 mg (yield: 87.2%) of the desired product.

Workup

  1. customwas carried out at room temperature
  2. filtration19 hours later, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-429e0ae8c2384c17acc91e83613e0a50
Source dataset
uspto-grants-1988_10
Patent number
US04778912

Reaction notes

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