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Technique for preparing N-carbobenzoxy-5 phenyl-L-cysteine

The technology of cysteine ​​and benzyloxycarbonyl is applied in the field of preparation technology of N-benzyloxycarbonyl-S-phenyl-L-cysteine, which can solve the problem of low quality of CBZ-PC products and high price of serine raw materials , can not meet user requirements and other problems, to achieve the effect of reduced production cost, good quality and convenient operation

Inactive Publication Date: 2005-08-31
高玉冠 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One is to use serine as a raw material, first protect N with benzyloxycarbonyl, and then synthesize N-benzyloxycarbonyl-L-serine-β lactone through Mitsunobu reaction, and then react with sodium thiophenate to obtain CBZ-PC, referred to as serine route, the CBZ-PC product synthesized by this route has high purity and content ≥ 99%, but the raw material of serine is expensive and the cost is high
Another method is to use L-cysteine ​​as raw material, react with diazonium salt in the presence of cuprous chloride, decopper and neutralize with sodium sulfide to prepare CBZ-PC, this method is referred to as diazonium, condensation route , in recent years, domestic and foreign focused research on diazo, condensation route, although this route L-cysteine ​​raw material is cheap, because the reaction yield of L-cysteine ​​and diazonium salt is too low (36%), The total yield of CBZ-PC is only 25%, and more importantly, the quality of CBZ-PC products is not high, and the content is only about 98%, which cannot meet user requirements (above 99%)

Method used

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  • Technique for preparing N-carbobenzoxy-5 phenyl-L-cysteine
  • Technique for preparing N-carbobenzoxy-5 phenyl-L-cysteine

Examples

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Embodiment 1

[0020] Dissolve 52g (28ml) of sulfuric acid in 275ml of water, add 22.5g of aniline solution, cool to below 5°C, dissolve 8.75g of sodium nitrite in 40ml of water, and add dropwise to the above solution to obtain aniline diazonium salt;

[0021] Dissolve 30g of L-cysteine ​​hydrochloride (0.17mol) containing one crystalline water in 225g of water, add 11g of 30% industrial hydrochloric acid, then add 4.25g of cuprous chloride, cool to below 5°C, and prepare the above Add the obtained diazonium salt into the solution dropwise, continue to react at this temperature for 6 hours after dropping, then raise the temperature of the reactant to 85°C-90°C, keep it warm for 1 hour, then cool to about 60°C and add sodium sulfide aqueous solution Suction filtration until no precipitate is formed, the solution is neutralized to PH5-7 with 30% sodium hydroxide, suction filtration, crude PC is dissolved in sodium hydroxide solution, 5g of activated carbon and reducing agent are added for decol...

Embodiment 2

[0024] Other methods are the same as in Example 1, except that 100 ml of toluene is added to the toluene-washed solution prepared in the same way as in Example 1, then acidified to PH2 with hydrochloric acid, stirred and crystallized at room temperature, and dried by suction to obtain 9.0 g of CBZ-PC , the content is 99.30%, the melting point is 93.5-94.5°C, and the yield is 89%.

Embodiment 3

[0026] Other methods are the same as in Example 1, except that the solution after washing with toluene obtained in the same way as in Example 1 is added with 5ml of carbon tetrachloride and 40ml of ethylene dichloride, acidified to PH2, cooled to 5 ° C, stirred and crystallized , filtered and dried to obtain 7.4g of CBZ-PC, with a content of 99.61%, a melting point of 94-95.5°C, and a yield of 73.4%.

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Abstract

A process for preparing N-benzoxycarbonyl-S-phenyl-L-cysteine includes synthesizing phenylamine diazonium salt from sodium nitrate and phenylamine, reacting on the solution of L-cysteine to obtain coarse S-phenyl-L-cysteine (PC), refining, dissolving, reacting on the solution of benzyl chloroformate, removing solvent, washing to obtain N-benzoxycarbonyl-S-phenyl-L-cysteine, adding solvent, acidifying, filter and baking. It can be used as the basic raw material for preparing anti-AIDS and antineoplastic medicines.

Description

technical field [0001] The invention relates to a new preparation process of N-benzyloxycarbonyl-S-phenyl-L-cysteine, the basic raw material of anti-AIDS and anti-tumor drugs. Background technique [0002] There are currently two methods for producing N-benzyloxycarbonyl-S-phenyl-L-cysteine ​​(CBZ-PC) products in the world. One is to use serine as a raw material, first protect N with benzyloxycarbonyl, and then synthesize N-benzyloxycarbonyl-L-serine-β lactone through Mitsunobu reaction, and then react with sodium thiophenate to obtain CBZ-PC, referred to as serine route, the CBZ-PC product synthesized by this route has high purity and content ≥ 99%, but the raw material of serine is expensive and the cost is high. Another method is to use L-cysteine ​​as raw material, react with diazonium salt in the presence of cuprous chloride, decopper and neutralize with sodium sulfide to prepare CBZ-PC, this method is referred to as diazonium, condensation route , in recent years, at...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/59
Inventor 高玉冠仲全福
Owner 高玉冠
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