Method for synthesizing d-biotin by catalytic double debenzylation

A biotin and compound technology, applied in the field of chemical synthesis of d-biotin, can solve the problems of complex d-biotin process steps, low yield and high cost

Active Publication Date: 2012-11-21
FUYANG KEXING BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The present invention aims to solve the problems of complex steps in the preparation of d-biotin in the prior art, low yield, high cost, and great adverse impact on the environment. The present invention provides a

Method used

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  • Method for synthesizing d-biotin by catalytic double debenzylation
  • Method for synthesizing d-biotin by catalytic double debenzylation
  • Method for synthesizing d-biotin by catalytic double debenzylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] 30 g of compound II was dissolved in 150 ml of ethanol and added to the autoclave. Then add 10% palladium carbon catalyst 3.0g, SO 4 2- / ZrO 2 -La solid superacid catalyst 1.5g, feed hydrogen until the pressure reaches 5.0MPa, heat to raise the temperature to 120°C, add hydrogen until the pressure is 7.5MPa, start the stirrer, control the rotating speed to 500rpm, and react for 6 hours . After the reaction, cool down and filter. The filtrate is retained and reused in the next production. After the filter residue was rinsed with ethanol, it was added to 50ml of 5% sodium carbonate solution, washed thoroughly, and then filtered. The filter residue is reused in production after washing and activation treatment. The filtrate was adjusted to about 1.0 with 5% sulfuric acid, and allowed to stand for crystallization. After filtering, the filter cake was washed, dried, and weighed to obtain 11.8 g of d-biotin. Converted into a molar yield of about 68%, the tested produc...

Embodiment 2~6

[0077] The steps of Example 1 were repeated, the amount of compound II fixed was 30 g, and other process conditions were changed. The results obtained are shown in Table 1 below.

[0078] Table 1 Embodiment 2~6 result

[0079]

Embodiment 7

[0080] Embodiment 7 Solvent and catalyst recycling experiment

[0081] Repeat Example 1, the process conditions are exactly the same as in Example 1, and the filtrate obtained by filtering after catalytic de-dibenzyl is analyzed for unreacted raw materials and the content of mono- and di-benzyl biotin, and after being converted into the amount of raw materials, add Compound II to 30g, add ethanol to 150ml. After the filter residue after alkali washing was activated, it was added to the high-pressure reactor for the second experiment, which was repeated four times. The results are shown in Table 2.

[0082] Table 2 Circular application experiment results

[0083]

[0084] It can be seen from Table 2 that after the solvent and the catalyst were recycled for 4 times, the performance did not deteriorate significantly, which shows that the method provided by the present invention has industrial practical value.

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Abstract

Disclosed is a method for synthesizing d-biotin by catalytic double debenzylation. The method is simple in process, high in yield and low in cost. The method includes: dissolving (3aS, 6aR)-hexahydro-2-oxo-1, 3-dibenzyl-1Hthieno [3, 4-d] imidazole-4-pentenoic acid into low molecular alcohol, adding mixed catalyst of Palladium-carbon and solid superacid, and feeding hydrogen for stirring reaction for 2-12 hours at 80-200 DEG C and 2.5-12.5 MPa; filtering after reaction, and washing residue with 1-20% (weight ratio) aqueous alkali; filtering, adjusting pH of filtrate to acidity, and standing for crystallization; and filtering to obtain the crystallized d-biotin. The method is applicable to production of the d-biotin.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to the chemical synthesis of d-biotin. Background technique [0002] Biotin, also known as vitamin H or coenzyme R, is a water-soluble B vitamin. It is widely distributed in animal and plant tissues, such as mainly in liver, kidney, egg yolk, yeast, and also in plant seeds, pollen, fresh vegetables and fruits. Biotin is an important vitamin. It is the prosthetic group of carboxylase and one of the important coenzymes in the intermediate metabolism of sugar, protein and fat. The lack of biotin in the human body can cause symptoms such as dermatitis, loss of appetite, nausea, vomiting, hair loss, anemia, elevated cholesterol, emotional depression, and weight loss. Biotin is also necessary for the normal growth and reproduction of poultry and livestock. The lack of biotin in poultry and livestock will lead to slow growth, reduced food intake and low feed conversi...

Claims

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Application Information

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IPC IPC(8): C07D495/04
Inventor 刘美星孙武军莫一平
Owner FUYANG KEXING BIOCHEM
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