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Method for preparing Boc-L-tyrosine by using (Boc)2O

A boc-l-, tyrosine technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbamate derivatives, etc., can solve the problems of low yield, difficult separation and purification, etc., and achieves simple and cost-effective methods. Inexpensive, high-yield effects

Inactive Publication Date: 2015-03-25
CHONGZHOU HERUI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has milder conditions, less pollution and harm, but it is easy to get N-Boc-L-tyrosine and N,O-(BOC) 2 The mixture of -L-tyrosine is extremely difficult to separate and purify, requires repeated crystallization, and the yield is low
[0008] In summary, there are certain defects and certain limitations in the methods for preparing Boc-L-tyrosine reported in the existing literature.

Method used

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  • Method for preparing Boc-L-tyrosine by using (Boc)2O

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1. Add 18.1g L-tyrosine and 100ml water into the reaction flask and stir. Add 5mol / L lye of 16g ​​sodium hydroxide configuration to adjust to alkaline. Then add 8g of (Boc) 2 O reacted for 1 hour, then added 8g of (Boc) 2 O was reacted for 1 hour, and finally 9g of (Boc) was added 2 O was reacted for 3 hours.

[0034] 2. Use petroleum ether 10ml / time to extract impurities three times. After adjusting the pH to 3 with 3mol / L hydrochloric acid, extract the product three times with ethyl acetate 0.5L / time. The combined ester layers were washed with brine until neutral. Add 15 g of anhydrous sodium sulfate and dry for 6 hours.

[0035] 3. Filtrate, concentrate the filtrate to dryness under reduced pressure, add 50ml petroleum ether and stir to crystallize. The product is centrifuged and dried. 25.9 g of product was obtained. Yield 92.17%.

Embodiment 2

[0037] 1. Add 1kgL-tyrosine and 5.5L water into the reaction flask and stir. Add 10mol / L lye of 884g potassium hydroxide configuration to adjust to alkaline. Then add 442g of (Boc) 2 O reacted for 2 hours, then added 442g of (Boc) 2 O reacted for 2 hours, and finally added 497g of (Boc) 2 O was reacted for 4 hours.

[0038] 2. Use n-hexane 500ml / time to extract impurities four times. After adjusting the pH to 3 with 6mol / L hydrochloric acid, extract the product four times with tert-butyl acetate 1L / time. The combined ester layers were washed with brine until neutral. Add 300 g of anhydrous sodium sulfate and dry for 8 hours.

[0039] 3. Filtrate, concentrate the filtrate to dryness under reduced pressure, add 2L of n-hexane and stir to crystallize. The product is filtered off and dried. The product 1402g was obtained. Yield 90.29%.

Embodiment 3

[0041] 1. Add 10kgL-tyrosine and 55L water into the reaction flask and stir. Add 7mol / L lye of 8.9kg potassium hydroxide configuration to adjust to alkaline. Then add 4.4kg of (Boc) 2 O reacted for 1 hour, then added 4.4kg of (Boc) 2 O reacted for 1 hour, and finally added 5kg of (Boc) 2 O was reacted for 3 hours.

[0042] 2. Use n-pentane 5L / time to extract impurities five times. After adjusting pH=3 with 5mol / L hydrochloric acid, extract the product five times with 10L / time of dichloromethane. The combined ester layers were washed with brine until neutral. Add 3 kg of anhydrous sodium sulfate and dry for 15 hours.

[0043] 3. Filtrate, concentrate the filtrate to dryness under reduced pressure, add 20L n-pentane and stir to crystallize. The product is filtered off and dried. 14.1 kg of product were obtained. Yield 90.77%.

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Abstract

The invention provides a synthetic method for Boc-L-tyrosine. According to the method, aqueous solution of one of L-tyrosine, sodium hydroxide and potassium hydroxide is added into (Boc)2O in batches under a one-pot condition, so that Boc-L-tyrosine is obtained in a high-yield mode by controlling the reaction condition. The method is low in cost, convenient and safe to operate, low in pollution, high in yield and easy for industrial production. A new method for industrially producing Boc-L-tyrosine is provided.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing Boc-L-tyrosine. Background technique [0002] Boc-L-tyrosine is mainly used in peptide synthesis, and it is an important intermediate of many peptide drugs that have been marketed or are about to be marketed at home and abroad. Such as anti-tumor drugs: leuprolide, goserelin, endocrine regulating drugs: lanreotide, gynecological drugs: carbetocin, etc. [0003] There are many ways to synthesize Boc-L-tyrosine, and the more common methods are as follows: [0004] a. L-tyrosine, Boc-N 3 , Triethylamine was obtained by reacting in DMF. But this method raw material Boc-N 3 It is easy to explode during the distillation and purification process, which is very dangerous. And the HN produced by the reaction 3 It is highly toxic and can cause shock. [0005] b. Obtained by reacting L-tyrosine, Boc-Cl, sodium hydroxide, and tetrahydrofuran in wa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/22C07C269/04
Inventor 郑果
Owner CHONGZHOU HERUI TECH
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