反应 #64412

反应方程式

tetrafluoroborate

L-carnitine

collidine

dichlorotetradecylphosphite

sodium metaperiodate

→

title compound

(R)-3-Carboxy-N,N,N-trimethyl-2-{[hydroxy(tetradecyloxy)phosphinyl]oxy}-1-propanaminium Hydroxide

溶剂

acetonitrile

water

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring at room temperature for two hours
2. 2
   过滤the reaction mixture is filtered through Celite
3. 3
   浓缩the filtrate is concentrated under vacuum
4. 4
   其他chromatographed on normal phase silica gel, initially with a 50/30/3 ratio of chloroform/methanol/concentrated ammonium hydroxide
5. 5
   其他with a 50/30/10 ratio of the same solvent system to yield a product that
6. 6
   其他flash chromatographed on LiChroprep RP-8 silica gel using gradients from water to acetonitrile and to methanol

实验过程

To a solution of 16.4 gm of the tetrafluoroborate salt of L-carnitine and 26 gm of collidine in 263 ml of acetonitrile is added 29.4 gm of dichlorotetradecylphosphite. The reaction mixture is stirred at room temperature for 17 hours and then a solution of 21.1 gm of sodium metaperiodate in 48.7 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 residue is flash chromatographed on normal phase silica gel, initially with a 50/30/3 ratio of chloroform/methanol/concentrated ammonium hydroxide and then with a 50/30/10 ratio of the same solvent system to yield a product that is then flash chromatographed on LiChroprep RP-8 silica gel using gradients from water to acetonitrile and to methanol. The title compound is isolated as an amorphous solid, (m.p. ~190° C. [dec]; 31P NMR=0.324 ppm; [α]25 =-10.34 C=1.0 MeOH).

来源