A kind of synthetic method of d-cycloserine

A synthesis method and cycloserine technology, applied in the direction of organic chemistry and the like, can solve the problems of low final yield, expensive raw materials, large energy consumption, etc., and achieve the effects of simple process, easier industrialization, and cost reduction.

A synthesis method and cycloserine technology, applied in the direction of organic chemistry and the like, can solve the problems of low final yield, expensive raw materials, large energy consumption, etc., and achieve the effects of simple process, easier industrialization, and cost reduction.

CN109734680BActive Publication Date: 2021-10-29NANJING REDWOOD FINE CHEM CO LTD
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  • A kind of synthetic method of d-cycloserine
  • A kind of synthetic method of d-cycloserine
  • A kind of synthetic method of d-cycloserine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Put 174g of R-3-chloroserine methyl ester hydrochloride in methanol, add 38ml of hydrochloric acid, then add 87.6g of acetone oxime, heat up to 45°C for 1 hour, cool down to 25°C, use sodium methoxide to maintain the pH to 8-9, React for 2 hours, filter to remove salt, and concentrate the mother liquor to a small volume to obtain the product D-cycloserine. (The quality of the obtained product D-cycloserine is 93.95g, the purity is 99.461%, and the yield is 91.53%).

Embodiment 2

[0040] Put 174g of R-3-chloroserine methyl ester hydrochloride in methanol, add 44ml of hydrochloric acid, then add 87.6g of acetone oxime, heat up to 55°C for 1 hour, cool down to 10°C, use sodium methoxide to maintain the pH to 8-9, React for 3 hours, filter to remove salt, and concentrate the mother liquor to a small volume to obtain the product D-cycloserine. (The quality of the obtained product D-cycloserine is 96.11g, the purity is 99.538%, and the yield is 93.71%).

Embodiment 3

[0042] Put 174g of R-3-chloroserine methyl ester hydrochloride in methanol, add 46ml of hydrochloric acid, then add 87.6g of acetone oxime, raise the temperature to 65°C for 1 hour, cool down to 5°C, and maintain the pH to 8-9 with sodium methoxide. React for 5 hours, filter to remove salt, and concentrate the mother liquor to a small volume to obtain the product D-cycloserine. (The quality of the product D-cycloserine obtained is 96.55g, the purity is 99.666%, and the yield is 94.25%).

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Abstract

The invention belongs to the field of drug synthesis, and discloses a synthetic method of D-cycloserine: add R-3-chloroserine methyl ester hydrochloride in methanol, add hydrochloric acid, then add acetone oxime, heat up the reaction, cool down, and use sodium methoxide to maintain pH to 8-9 to react, filter to remove salt, concentrate to a small volume to obtain D-cycloserine in one step. The method has the advantages of simple process operation, environmental friendliness, mild reaction conditions, a final product purity of up to 99%, and a yield of up to 94.25%, which is beneficial to industrial production.

Description

technical field [0001] The invention relates to a preparation method of the new drug Sofosbuvir intermediate D-cycloserine for the treatment of chronic hepatitis C. Background technique [0002] D-cycloserine, also known as D-4-amino-3-oxazolidinone, is an antibiotic drug that has a good inhibitory effect on Mycobacterium tuberculosis. Because bacteria are not easy to develop drug resistance to it, it is mainly used clinically to treat the infection of drug-resistant Mycobacterium tuberculosis. In addition, studies have found that D-cycloserine is a special regulator of excitatory amino acid NMDA (N-methyl-D-aspartate) receptors in the central nervous system, and it is effective in the treatment of psychological phobias, depression, schizophrenia, etc. Disease also has a good auxiliary effect, and it is also an important intermediate in the synthesis of atypical β-lactam antibiotic Lactivicin. Therefore, D-cycloserine has wide application prospects and huge market demand. ...

Claims

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Application Information

Patent Timeline
29 Oct 2021
Publication
CN109734680B
IPC
C07D261/04
Inventors
吴法浩; 李钢