Thiazole → (2RS)-3-Hexadecyloxy-2-(5-phenyl-3-isoxazolyloxy)propyl 2-thiazolioethyl phosphate
Reaktionsgleichung
[P:1]([O-:40])([O:36][CH2:37][CH2:38]Br)([O:3][CH2:4][CH:5]([O:24][C:25]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:27][N:26]=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][CH3:23])=[O:2].[S:41]1[CH:45]=[CH:44][N:43]=[CH:42]1>C1(C)C=CC=CC=1>[P:1]([O-:40])([O:36][CH2:37][CH2:38][C:42]1[S:41][CH:45]=[CH:44][NH+:43]=1)([O:3][CH2:4][CH:5]([O:24][C:25]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:27][N:26]=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][CH3:23])=[O:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 0.925 g of the crude (2RS)-3-hexadecyloxy-2-(5-phenyl-3-isoxazolyloxy)propyl 2-bromoethyl phosphate obtained as described in the first part of Example 7 and 0.51 ml of thiazole in 0.8 ml of toluene was heated on an oil bath kept at 70° C. for 5 days, whilst stirring. The mixture was then cooled and freed from toluene by evaporation under reduced pressure. 15 ml of chloroform were then added to the residue, followed by 0.296 g of silver carbonate. The mixture was then heated under reflux for 1 hour. At the end of this time, the mixture was cooled, an insoluble material was filtered off and the solvent was stripped off from the filtrate by evaporation under reduced pressure. The residue was subjected to column chromatography through 20 g of silica gel. 0.117 g of the title compound was obtained as a viscous oil from the fractions eluted with a 1:1 by volume mixture of methanol and methylene chloride and with a 35:60:5 by volume mixture of methanol, methylene chloride and water.