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Method for preparing 2-P-octyl-phenenl-2-amino-propanediol hydrochloride

A technology of aminopropylene glycol hydrochloride and diethyl acetamidomalonate, which is applied in the field of medicinal immunosuppressants, can solve the problems of low total yield, high cost, and long reaction steps, and achieve high total yield, The effect of low production cost and short production cycle

Inactive Publication Date: 2006-08-09
NANJING YOKO PHARMA GRP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of this invention is to provide a kind of method for preparing 2-p-octylphenethyl-2-aminopropanediol hydrochloride, overcome the long reaction steps in the background technology, the deficiency that the total yield is low cost and high

Method used

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  • Method for preparing 2-P-octyl-phenenl-2-amino-propanediol hydrochloride
  • Method for preparing 2-P-octyl-phenenl-2-amino-propanediol hydrochloride

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Embodiment

[0023] One, the preparation of compound p-octanoylstyrene (III):

[0024] At 0°C, add octanoyl chloride to a suspension of dichloromethane (200ml) in aluminum trichloride (32g, 0.24mol), stir at 0-5°C for 0.5h after the addition, add dropwise (II) (20g, 0.19mol), the ice-salt bath was removed after the dropwise addition, stirred at room temperature for 3h, and the end point was detected by TLC. The mixture was poured into ice water, and the organic layer was separated. The aqueous layer was extracted with dichloromethane (20ml×3). Wash with brine, dry the organic layer with anhydrous sodium sulfate, filter, evaporate the solvent, and recrystallize from a mixed solvent of petroleum ether and ethyl acetate (3:1) to obtain 39.35 g of p-octanoylstyrene (III) as colorless crystals , melting point 62-64°C, yield 90%.

[0025] 1 H NMR (CDCl 3 )δ: (d, J = 9.6Hz, 2H), 7.47 (d, 9.6Hz, 2H), 4.74 (dd, J = 13.2, 21.0Hz, 1H), 5.86 (d, J = 21.0Hz, 1H), 5.37(d, J=13.2Hz, 1H), 2.93(t, J=9....

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Abstract

The invention offers 2-amphi capryl phenethyl-2-amino group propylene glycol hydrochloride preparation method. It includes the following steps: doing Friedel-Crafts reaction for styrene and capryl chloride to produce amphi capryl styrene; doing Michael addition reaction with kharophen diethyl malonate under alkali action to produce 2-amphi capryl phenethyl-2-kharophen diethyl malonate; reacting with triethyl silane to produce 2-amphi capryl phenethyl-2-kharophen diethyl malonate; reducing and hydrolyzing to produce 2-amphi capryl phenethyl-2-amino group propylene glycol; acidifying with hydrochloric acid to produce salt. It has the advantages of simple line, low cost, short period, little pollution, and high yield. It also offers the intermediate compound preparation method.

Description

technical field [0001] The invention relates to a method for preparing 2-p-octylphenethyl-2-aminopropanediol hydrochloride, which belongs to medicinal immunosuppressants. Background technique [0002] 2-p-octylphenethyl-2-aminopropanediol (FTY720 for short) and its salts are immunosuppressants and are currently undergoing clinical research. The results of pharmacological experiments show that the compound has good effects in the experiments of liver transplantation in rats, small intestine transplantation and kidney transplantation in dogs. In terms of combination therapy, the combination of FTY720 and subactive therapeutic dose of CsA can prolong the survival time of grafts, and the same result can be observed in combination with FK506 or RAD, and shows a synergistic effect, which is better than that of cyclosporin or CsA alone. FTY720 etc. more significantly inhibit the immune rejection of transplanted organs. Moreover, the toxicity of this co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/00C07C215/28
Inventor 王玉成季刚辜顺林张雪梅李磊陈玉芳
Owner NANJING YOKO PHARMA GRP CO LTD
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