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Synthesis method of mycophenolic acid-13CD3

A synthesis method, mycophenolic acid technology, applied in the fields of organic chemistry, organic chemistry, bulk chemical production, etc., can solve the problems of long reaction route, high cost, long route, etc., and achieve the effect of controllable cost

Active Publication Date: 2020-05-15
南京昊绿生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] If the method of synthesizing mycophenolic acid is adopted, the method of synthesizing mycophenolic acid- 13 CD3 has the following technical problems: total synthesis method, long route, expensive and difficult to obtain raw materials, huge cost, and no operability
[0007] This synthesis method is more feasible. Use commercially available mycophenolic acid to protect the phenolic hydroxyl group, and then remove the methyl protecting group. Through this method, mycophenolic acid can be synthesized- 13 CD3, but the reaction route is longer

Method used

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  • Synthesis method of mycophenolic acid-13CD3
  • Synthesis method of mycophenolic acid-13CD3
  • Synthesis method of mycophenolic acid-13CD3

Examples

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Embodiment 1

[0031] Example 1 Synthesis of mycophenolic acid- 13 CD3

[0032] step 1)

[0033] The synthetic route is as follows:

[0034]

[0035] N 2 Under protection, 7.5g (23.4mmol) of compound 1, 15mL pyridine (186.4mmol), 74mL 2,4,6-collidine (560mmol), and 21.2g (158.4mmol) of lithium iodide were sequentially added to a 250 mL single-necked bottle 48 hours at 135°C, followed by plate monitoring. After the reaction of the raw materials was complete, cool the system and adjust the pH to about 4 with dilute hydrochloric acid, then extract with ethyl acetate, combine the organic phases, and wash the organic phases once with 0.1M dilute hydrochloric acid. Washed once with saturated brine, dried over anhydrous sodium sulfate, and spin-dried the solvent to obtain 7.5 g of a light yellow solid with a yield of 95.6%. The reaction product was directly used in the next reaction.

[0036] step 2)

[0037] The synthetic route is as follows:

[0038]

[0039] Dissolve 7.0g (22.8mmol) ...

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Abstract

The invention provides a synthesis method of mycophenolic acid-13CD3, which comprises the following steps: (1) carrying out a demethylation reaction on a compound 1, lithium iodide, pyridine and 2, 4,6-trimethylpyridine under the protection of N2 to obtain a compound 2; (2) carrying out an esterification reaction on the compound 2 and thionyl chloride in a methanol system to obtain a compound 3;(3) carrying out a light delay reaction on the compound 3, triphenylphosphine, diethyl azodicarboxylate and methanol-13CD3 in anhydrous tetrahydrofuran to obtain a compound 4; and (4) carrying out anester hydrolysis reaction on the compound 4 and lithium hydroxide monohydrate in a methanol / water system to obtain mycophenolic acid-13CD3. According to the synthesis method of mycophenolic acid-13CD3disclosed by the invention, a target molecule is successfully synthesized by using a relatively short synthesis route, and the cost is controllable.

Description

technical field [0001] The present invention relates to a kind of mycophenolic acid- 13 A CD3 synthesis method belongs to the technical field of chemical synthesis. Background technique [0002] Mycophenolic acid, also known as mycophenolic acid, as the main immunosuppressant has been widely used at home and abroad to prevent and treat acute rejection of transplanted organs. Mycophenolate mofetil exerts immunosuppressive activity in vivo through conversion to mycophenolic acid. In different transplant populations, great differences in the pharmacokinetics of mycophenolic acid can be found among individuals, and internal and external factors can affect its pharmacokinetics. Mycophenolate mofetil (MMF) is a 2-morpholinoethyl ester derivative of mycophenolic acid (MPA). MPA can non-competitively bind hypoxanthine mononucleotide dehydrogenase (IMPDH), which is the key enzyme for the de novo synthesis of guanine nucleotides in the process of T and B lymphocyte proliferation. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88
CPCC07D307/88C07B2200/05Y02P20/55
Inventor 贲昊玺于海涛孙爱学
Owner 南京昊绿生物科技有限公司
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