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A kind of purification method of biotin intermediate

A purification method and intermediate technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult crystallization, impurity cannot be removed, affecting production and quality, etc.

Active Publication Date: 2019-01-11
安徽泰格生物技术股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Biotin Intermediate (3aS,6aR)-1,3-Dibenzyl-4-ene-tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-n-pentanoic acid It is a key intermediate for the synthesis of biotin. It has been reported in the literature for a long time that its properties are semi-solid paste at room temperature, difficult to crystallize, and its content can only reach below 95%, resulting in some impurities that cannot be removed. production and quality of each step

Method used

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  • A kind of purification method of biotin intermediate
  • A kind of purification method of biotin intermediate
  • A kind of purification method of biotin intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Take (3aS, 6aR)-1,3-dibenzyl-4-ene-tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-n-pentanoic acid crude product 60g ( The content is 80.15%, the molecular weight is 422.54), add 20ml of anhydrous methanol, ultrasonically heat and dissolve, after it is completely dissolved, add 1ml of 98% concentrated sulfuric acid, react in a water bath at 55°C for 4h, cool to 20°C, wash with saturated sodium carbonate solution Washing liquid three times, 50ml each time, to remove non-ester and acidic impurities. Discard the water layer, take the organic layer, first add 60ml of methanol to it, then slowly drop 60ml of distilled water, and slowly cool down to 0-2°C, the cooling rate does not exceed 0.5°C / min, after the addition of distilled water is completed, put After the material was placed at -5°C and stirred for 3 hours, a large number of crystals (the esterified compound II) appeared, filtered, and washed twice with 25ml of 50% ice methanol to obtain pale yellow needle-shaped cr...

Embodiment 2

[0041] Change the 20ml of anhydrous methanol in Example 1 to 10ml of anhydrous methanol, and the remaining material consumption and operation method remain unchanged.

Embodiment 3

[0043] The 1ml concentrated sulfuric acid in the embodiment 1 is changed into 0.5ml concentrated sulfuric acid, and all the other material consumptions and operating methods are unchanged.

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Abstract

The invention discloses a method for purifying biotin midbody. The derivative thereof, namely, (3aS, 6aR)-1,3-dibenzyl-4-alkene-tetralin-1H-thieno [3,4-d] imidazole-2(3H)-ketone-4-ethyl-n-valerate can generate needle-shaped crystal, the impurities are removed and the content of (3aS, 6aR)-1,3-dibenzyl-4-alkene-tetralin-1H-thieno [3,4-d] imidazole-2(3H)-ketone-4-ethyl-n-valerate can be increased to 95% or above. The method also can be used as an optional method for removing impurities for difficult crystallized monocarboxylic acid and amorphous organic acid crystal without aromaticity.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, in particular to a biotin intermediate (3aS,6aR)-1,3-dibenzyl-4-ene-tetrahydro-1H-thieno[3,4-d]imidazole-2 Purification method of (3H)-keto-4-n-pentanoic acid. Background technique [0002] Biotin, also known as vitamin H and coenzyme R, is a water-soluble vitamin and also belongs to the vitamin B family. It is a necessary substance for the synthesis of vitamin C and is indispensable for the normal metabolism of fat and protein. It is a necessary nutrient to maintain the natural growth, development and normal human body function and health of the human body. [0003] Biotin Intermediate (3aS,6aR)-1,3-Dibenzyl-4-ene-tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one-4-n-pentanoic acid It is a key intermediate for the synthesis of biotin. It has been reported in the literature for a long time that its properties are semi-solid paste at room temperature, difficult to crystallize, and its ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 王珂
Owner 安徽泰格生物技术股份有限公司