Ethanolamine → Monosodium 2-(2-hydroxy-3-tetradecyloxypropylamino)ethyl phosphate

HRID 1106

Reaction equation

HRID 1106 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH:6]([OH:23])[CH2:7][O: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][CH3:22].C(OCCCCCCCCCCCCCC)C1OC1.C(CN)O.O1CCCC1.[P:52](=O)([OH:55])([OH:54])[OH:53].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+:72].[Na]>O>[P:52]([OH:55])([O-:54])([O:1][CH2:2][CH2:3][NH:4][CH2:5][CH:6]([OH:23])[CH2:7][O: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][CH3:22])=[O:53].[Na+:72]

Participants

10

Reactant 8

HCID 700EthanolamineHCID 1004Phosphoric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 38190Oxirane, 2-((tetradecyloxy)methyl)-HCID 5360545SodiumHCID 124588633-(2-Hydroxyethylamino)-1-tetradecyloxy-2-propanol

Product 1

HCID 88302415Monosodium 2-(2-hydroxy-3-tetradecyloxypropylamino)ethyl phosphateYield 36.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 300-ml flask equipped with a stirrer was charged with 5.13 g (14.8 mmol) of 3-(2-hydroxyethylamino)-1-tetradecyloxy-2-propanol prepared from tetradecyl glycidyl ether and ethanolamine in the same manner as in Preparation Example 14, and 70 mol of tetrahydrofuran, 1.95 g (16.9 mmol) of 85% phosphoric acid and 3.54 g (30.7 mmol) of P2O5 were added thereto. The resultant mixture was stirred at 65° C. for 10 hours. After cooling the mixture to room temperature, 0.56 g of water was added to the mixture, stirring was conducted for 30 minutes, 5.0 g of 48% aqueous NaOH were added further. After concentrating the resultant reaction mixture under reduced pressure, the resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor. The resultant extract was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel, thereby obtaining 2.32 g (yield: 34.9%) of the title compound monosodium (IIa-14).

Workup

  1. customA 300-ml flask equipped with a stirrer
  2. additionwere added
  3. concentrationAfter concentrating the resultant
  4. customreaction mixture under reduced pressure
  5. extractionthe resultant residue was subjected to extraction with ethanol by means of a Soxhlet's extractor
  6. extractionThe resultant extract
  7. concentrationwas concentrated under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1c432984f9d54ac78349420a214a1024
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Linked notes

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