Synthesis method of N-omega-nitro-L-benzyl arginine hydrochloride

A kind of technology of arginine benzyl ester hydrochloride and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as unfavorable mass production, high cost, and many steps, and reduce production And the effect of follow-up processing cost, low raw material cost, and less solvent amount

Inactive Publication Date: 2017-05-10
GL BIOCHEM SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the technical problems that benzyl bromide, the raw material of the existing synthesis method, is very irritating, not conducive to environmental protection, has many steps and high cost, and is not conducive to mass production

Method used

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  • Synthesis method of N-omega-nitro-L-benzyl arginine hydrochloride
  • Synthesis method of N-omega-nitro-L-benzyl arginine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] a. Mix 100g Boc-Arg(NO 2 )-OH (319.3 313.19nmol) suspended in 500ml benzyl alcohol;

[0017] b. Add 111.78g SOCl dropwise at 5°C 2 (118.97 939.57 nmol);

[0018] C. Insulate at 5-8°C and stir for 48 hours;

[0019] d. At 10°C, add methanol 100ml, diethyl ether 500ml, stir and crystallize, and dry to obtain crude product 108.55g H-Arg(NO 2 )-obzl.hcl;

[0020] e. The solid was dissolved by heating with 325.65ml of methanol, and crystallized by adding 976.95ml of ether after cooling;

[0021] Filter and dry to get 80g fine product with a rate of 73.7%. The structure was confirmed to be correct by infrared and NMR, see figure 1 , figure 2 .

Embodiment 2

[0023] a. Mix 100g Boc-Arg(NO 2 )-OH (319.3 313.19nmol) suspended in 500ml benzyl alcohol;

[0024] b. Add 74.52g SOCl dropwise at 0°C 2 (118.97 626.38 nmol);

[0025] c. Insulate at 5-8°C and stir for 48 hours;

[0026] d. At 10°C, add 100ml of methanol and 500ml of diethyl ether to stir and crystallize, and dry to obtain 90g of crude product H-Arg(NO 2 )-obzl.hcl;

[0027] e. The solid was dissolved by heating with 270ml of methanol, and crystallized by adding 810ml of ether after cooling;

[0028] Filtration and drying to obtain 50g of fine product yield 46%. The structure was confirmed to be correct by infrared and NMR, see figure 1 , figure 2 .

Embodiment 3

[0030] a. Mix 100g Boc-Arg(NO 2 )-OH (319.3 313.19nmol) suspended in 500ml benzyl alcohol;

[0031] b. Add 111.78g SOCl dropwise at 5°C 2 (118.97 939.57 nmol);

[0032] c. Insulate at 5-8°C and stir for 24 hours;

[0033] d. At 10°C, add 100ml of methanol and 500ml of diethyl ether, stir and crystallize, and dry to obtain 95g of crude product h-arg(no2)-obzl.hcl

[0034] e. The solid is dissolved by heating with 285ml of methanol, and crystallized by adding 855ml of ether after cooling

[0035] Filtration and drying yielded 68g of fine product, yield 62.6%. The structure was confirmed to be correct by infrared and NMR, see figure 1 , figure 2 .

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Abstract

The invention relates to a synthesis method of an N-omega-nitro-L-benzyl arginine hydrochloride. The technical problems that an existing synthesis method is quite high in the pungency of a raw material benzyl bromide, is not beneficial to environment protection, is multiple in steps and high in cost and is also not beneficial to mass production are mainly solved. According to the technical scheme provided by the invention, the synthesis method of the N-omega-nitro-L-benzyl arginine hydrochloride is characterized by comprising the following steps of I, suspending Boc-Arg(NO2)-OH in benzyl alcohol at room temperature; II, dropwise adding SOCl2 into an obtained first mixture at low temperature; III, keeping temperature at 5 to 8 DEG C after the SOCl2 is completely dripped, agitating and making an obtained second mixture react for 24 to 48 hours; IV, adding methanol and diethyl ether into an obtained third mixture at the low temperature, and crystallizing an obtained fourth mixture; V, refining a crystallized substance by using the methanol and the diethyl ether to obtain a final product. The invention provides a method for producing the N-omega-nitro-L-benzyl arginine hydrochloride on a large scale.

Description

technical field [0001] The present invention relates to the synthesis method of N-omega-nitro-L-arginine benzyl ester hydrochloride. Background technique [0002] The synthetic method of existing preparation N-omega-nitro-L-arginine benzyl ester hydrochloride is generally: the first step, Boc-Arg (NO 2 )-OH was suspended in ethyl acetate. In the second step, benzyl bromide and triethylamine are added. The third step is to reflux overnight. The 4th step, filter and handle and get Boc-Arg (NO 2 ) - obzl solid. In the fifth step, the solid is refluxed with HCl and dichloromethane, and processed to obtain H-Arg (NO 2 )-obzl.hcl. The synthesis conditions of this method are relatively harsh, and the raw material benzyl bromide is very irritating, which is not conducive to environmental protection. The subsequent treatment requires professional equipment, and the steps are many and the cost is high, which is also not conducive to mass production. Contents of the invention ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C277/08C07C279/14
CPCC07C277/08C07C279/14
Inventor 吴福全周国峰林崔建徐红岩
Owner GL BIOCHEM SHANGHAI
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