2,4,6-Trimethylpyridine → N,N,N-trimethyl-4-oxo-4-[(2-propenyl)oxyl]-2-[{hydroxy(tetradecyloxy)phosphinyl}oxy]-1-butanaminium hydroxide

HRID 439756

Reaktionsgleichung

Reaktionsgleichung von HRID 439756
F[B-](F)(F)F.[OH:6][C@H:7]([CH2:13][C:14](=[O:16])[O-:15])[CH2:8][N+:9]([CH3:12])([CH3:11])[CH3:10].N1C(C)=CC(C)=[CH:19][C:18]=1[CH3:25].Cl[CH:27](Cl)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][P:42]([O-:44])[O-:43].I([O-])(=O)(=O)=O.[Na+]>C(#N)C.O>[OH-:6].[CH3:11][N+:9]([CH3:12])([CH3:10])[CH2:8][CH:7]([O:6][P:42]([OH:44])([O:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH3:27])=[O:43])[CH2:13][C:14](=[O:15])[O:16][CH2:25][CH:18]=[CH2:19]

Komponenten

8

Edukt 5

HCID 79532,4,6-TrimethylpyridineHCID 10917(-)-CarnitineHCID 26255TetrafluoroborateHCID 23667635Sodium periodateHCID 86748667Dichlorotetradecylphosphite

Produkt 1

HCID 22407898N,N,N-trimethyl-4-oxo-4-[(2-propenyl)oxyl]-2-[{hydroxy(tetradecyloxy)phosphinyl}oxy]-1-butanaminium hydroxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 3.6 gm of the tetrafluoroborate salt of the allyl ester of L-carnitine and 4.5 gm of collidine in 25 ml of acetonitrile is added 5.7 gm of dichlorotetradecylphosphite in 25 ml of acetonitrile. The reaction mixture is stirred at room temperature for 17 hours, and then a solution of 4 gm of sodium metaperiodate in 20 ml of water is added. After stirring at room temperature for two hours, the reaction mixture is filtered through Celite; and the filtrate is concentrated under vacuum. The resulting residue is flash chromatographed on silica gel, initially with a 50/30/5 ratio of methylene chloride/methanol/ concentrated ammonium hydroxide and then with a 50/30/8 ratio of the same solvent system. Subsequent flash chromatography on LiChroprep RP-8 silica gel eluting initially with water and then with methanol gave N,N,N-trimethyl-4-oxo-4-[(2-propenyl)oxyl]-2-[{hydroxy(tetradecyloxy)phosphinyl}oxy]-1-butanaminium hydroxide, inner salt as an amorphous solid (31P NMR=0.108 ppm).

Aufarbeitung

  1. stirringAfter stirring at room temperature for two hours
  2. filtrationthe reaction mixture is filtered through Celite
  3. concentrationand the filtrate is concentrated under vacuum
  4. customchromatographed on silica gel, initially with a 50/30/5 ratio of methylene chloride/methanol/ concentrated ammonium hydroxide

Quellen und Nachweise

ORD-Eintrag
ord-a156936a5608417b8112cd3554f37061
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516767

Verknüpfte Notizen

Wird geladen…