Pyridine → Oleyloxyethyl phosphorylcholine

HRID 1719794

Reaktionsgleichung

Reaktionsgleichung von HRID 1719794
[CH2:1]([O:19][CH2:20][CH2:21][OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[P:23](Cl)(Cl)(=[O:28])[O:24]CCBr.[N:31]1[CH:36]=CC=C[CH:32]=1.[CH:37](Cl)(Cl)Cl.[CH3:41][C:42](C)=[O:43]>C1C=CC=CC=1>[P:23]([O-:24])([O:43][CH2:42][CH2:41][N+:31]([CH3:36])([CH3:37])[CH3:32])([O:22][CH2:21][CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:28]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 4684632(2-Bromoethoxy)phosphonoyl dichlorideHCID 5364713EmulphorHCID 15930782Chloroform acetone

Produkt 1

HCID 13116658Oleyloxyethyl phosphorylcholineAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

In benzene were dissolved 4.0 g of 2-[(Z)-9-octadecen-1-yl)oxyethanol and 4.6 g of 2-bromoethyl phosphorodichloridate, and following dropwise addition of 1.5 g of pyridine under ice-cooling, the mixture was stirred at room temperature. The reaction mixture was treated by the procedure of Production Example 1 including hydrolysis, quaternization, purification by silica gel column chromatography and recrystallization from chloroform-acetone to give 0.52 g (9%) of the desired product.

Aufarbeitung

  1. temperaturecooling

Quellen und Nachweise

ORD-Eintrag
ord-686d7471b1af47a4967c586248a8bbef
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04542219

Verknüpfte Notizen

Wird geladen…