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Preparation method of BOC-L-asparagine

A technology of asparagine and asparagine, which is applied in the field of medicinal chemistry, can solve the problems of unfavorable industrialization, cumbersome operation, cost, environmental protection, and high safety, and achieve the effect of being conducive to industrialized production, simple operation, and high safety factor

Active Publication Date: 2016-12-07
宜兴市前成生物有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method has mild reaction conditions and a short time, and can obtain higher yields, triethylamine has a strong ammonia smell, and due to the use of an organic solvent-water solvent system, the follow-up operations are cumbersome, and after the reaction needs to be Evaporation of organic solvents, followed by extraction, water layer acid adjustment, extraction, and crystallization is not conducive to industrialization, and the cost, environmental protection, and safety requirements are also extremely high

Method used

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  • Preparation method of BOC-L-asparagine
  • Preparation method of BOC-L-asparagine
  • Preparation method of BOC-L-asparagine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] BOC-L-asparagine was prepared according to the following preparation steps:

[0026] Step (1), put 150g L-Asn (1mol), 240g di-tert-butyl dicarbonate (1.1mol) and 700mL water into the 3L flask; at a temperature of 25~30°C, under the condition that the rotation speed is maintained at 120 rpm , 300mL of 10mol / L NaOH aqueous solution (3mol) was added dropwise while stirring, and the rate of addition was controlled to make pH=9~10. During this process, L-Asn and di-tert-butyl dicarbonate were dissolved in water and reacted; the dropwise addition was completed. After that, the temperature was raised to 34°C, and the reaction was continued for 4 hours under stirring;

[0027] Step (2), the reaction solution is cooled to less than 10°C with ice brine; 6mol / L hydrochloric acid is slowly added dropwise, the temperature is kept lower than 10°C during the dropwise addition, acidified to pH4.3, and the BOC-L-asparagine crude product is separated out, Suction filtration, wash the so...

Embodiment 2

[0029] BOC-L-asparagine was prepared according to the following preparation steps:

[0030] Step (1), put 150g L-Asn (1mol), 262g di-tert-butyl dicarbonate (1.2mol) and 700mL water into the 3L flask; at a temperature of 25~30°C, under the condition that the rotation speed is maintained at 120 rpm , 300mL of 10mol / L NaOH aqueous solution (3mol) was added dropwise while stirring, and the rate of addition was controlled to make pH=9~10. During this process, L-Asn and di-tert-butyl dicarbonate were dissolved in water and reacted; the dropwise addition was completed. After that, the temperature was raised to 34°C, and the reaction was continued for 4 hours under stirring;

[0031] Step (2), the reaction solution is cooled to less than 10°C with ice brine, and residual (Boc) is detected 2 O crystals; slowly add 6mol / L hydrochloric acid dropwise, keep the temperature below 10 °C during the dropwise addition, acidify to pH 4.3, separate out the crude BOC-L-asparagine, filter with suc...

Embodiment 3

[0033] BOC-L-asparagine was prepared according to the following preparation steps:

[0034] 150g L-Asn (1mol), 218g di-tert-butyl dicarbonate (1mol) and 700mL water were put into the step (1), 3L flask; at a temperature of 25~30°C, under the condition that the rotation speed was maintained at 120 rev / min, 300mL of 10mol / L NaOH aqueous solution (3mol) was added dropwise while stirring, and the rate of addition was controlled to make pH=9~10. During this process, L-Asn and di-tert-butyl dicarbonate were dissolved in water and reacted; the dropwise addition was completed. After that, the temperature was raised to 34°C, and the reaction was continued for 4 hours under stirring;

[0035] Step (2), the reaction solution is cooled to less than 10°C with ice brine, and residual (Boc) is detected 2 O crystal; slowly add 6mol / L hydrochloric acid dropwise, keep the temperature below 10°C during the dropwise addition, acidify to pH 4.3, separate out the crude BOC-L-asparagine, filter wit...

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Abstract

The invention discloses a preparation method of BOC-L-asparagine. The preparation method comprises the following steps: using L-asparaginate and di-tert-butyl dicarbonate ester as raw materials and water as a reaction solvent to carry out a reaction under the alkaline condition of pH 9-10 to generate BOC-L-asparagine, acidizing a reaction liquid to pH 4.0-4.5 to precipitate out a BOC-L-asparagine crude product, carrying out suction filtration, washing with water and drying to obtain a BOC-L-asparagine refined product. The preparation method of BOC-L-asparagine has advantages of mild reaction condition, fast reaction and lower cost of raw materials. As water is used as the reaction solvent, the subsequent operation is simple, and BOC-L-asparagines crystal can be precipitated out only by acidifying. The method is beneficial to industrial production, is environment friendly and has high safety factor.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of BOC-L-asparagine. Background technique [0002] L-asparagine is used to synthesize organic raw materials or pharmaceutical intermediates. When using L-asparagine to synthesize and design, it is often necessary to protect the amine group. Boc (tert-butoxycarbonyl) is a good amino group. Protecting groups have been widely used in synthetic design. BOC-L-Asparagine (BOC-L-Asparagine), also known as: N-tert-butoxycarbonyl-L-asparagine, white crystalline substance, soluble in DMF, insoluble in petroleum ether. Molecular formula: C 9 H 16 N 2 O 5 ; The structure is as follows: [0003] [0004] Qiu Chuanliang et al. investigated the Boc conversion of amino dibasic acids. Iminodiacetic acid and aspartic acid were combined with (Boc) in an alkaline 1,4-dioxane-water solvent system. 2 O reaction and glutamic acid with (Boc) in basic 1,4-diox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/22
CPCC07C269/04C07C271/22
Inventor 席日新刘涛
Owner 宜兴市前成生物有限公司
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