2,4,6-Trimethylpyridine → (R)-3-Carboxy-N,N,N-trimethyl-2-{[hydroxy(tetradecyloxy)phosphinyl]oxy}-1-propanaminium Hydroxide

HRID 36134

반응식

HRID 36134 반응식
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)=CC=1C.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].[C:14]([CH2:13][C@@H: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])[CH2:8][N+:9]([CH3:12])([CH3:10])[CH3:11])([OH:15])=[O:16]

참가 물질

8

반응물 5

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

생성물 1

HCID 86748666(R)-3-Carboxy-N,N,N-trimethyl-2-{[hydroxy(tetradecyloxy)phosphinyl]oxy}-1-propanaminium Hydroxide

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f07963c8584147a5b1e3af067d4981b6
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412137

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