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

HRID 36143

반응식

HRID 36143 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)=[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5d503d989a5f46a2abc2f26468da3fcb
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412137

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