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

A technology of aminopropanediol hydrochloride and diethyl acetamidomalonate is applied in the field of medicinal immunosuppressants, can solve the problems of long reaction steps, low total yield and high cost, and achieves low production cost and total yield. The effect of high rate and short production cycle

Inactive Publication Date: 2009-10-14
NANJING YOKO PHARMA GRP CO LTD
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  • 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

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Embodiment

[0028] One, the preparation of compound p-octanoylstyrene (III):

[0029] 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%.

[0030] 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 provides a method for preparing 2-p-octylphenethyl-2-aminopropanediol hydrochloride: the method comprises the following steps: styrene (II) and octanoyl chloride carry out Friedel-Crafts reaction to generate p-octanoyl Styrene (III); (III) carries out Michael addition reaction with acetamidodiethyl malonate under alkali action, generates 2-to-octanoylphenethyl-2-acetamidodiethyl malonate (IV ); (IV) reacts with triethylsilane to generate 2-to-octylphenethyl-2-acetamidodiethyl malonate (V); (V) generates 2-to-octylphenethyl through reduction and hydrolysis Base-2-aminopropanediol (VI), then acidified with hydrochloric acid to form a salt to obtain the product of the present invention. The invention has the advantages of short route, low cost, short cycle, less pollution and high yield. At the same time, the preparation method of the intermediate in the above preparation process is also provided.

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 compound is significantly lowe...

Claims

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Application Information

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Patent Type & Authority Patents(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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