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Preparation method of R-lansoprazole

A technology of dexlansoprazole and organic solvents, applied in the field of compound preparation, can solve the problems of low product ee value, unfavorable separation and recovery, and low product yield, so as to overcome instability, improve yield and optical purity , the effect of increasing productivity

Inactive Publication Date: 2017-11-28
赛隆药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of asymmetric catalytic oxidation synthesis, the titanium catalyst Ti(i-PrO) 4 Cooperate with the ligand L-diethyl tartrate to form a titanium catalyst complex, which is stable and unfavorable for separation and recovery, resulting in low yield of synthesized products and low ee value of the product

Method used

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  • Preparation method of R-lansoprazole
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  • Preparation method of R-lansoprazole

Examples

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Embodiment 1

[0027] A kind of preparation method of dexla soprazole, this method comprises the steps: dissolve 2.84g tetraisopropyl titanate with 25mL organic solvent, be made into tetraisopropyl titanate solution, dissolve 8.02g titanium with 50mL organic solvent Catalyst ligand, be made into titanium catalyst ligand solution, dissolve the compound of formula one of 3.53g with the organic solvent of 25mL, be made into the compound solution of formula one; Organic solvent is the mixture of toluene and DMF that volume ratio is 2:5; At ℃, add tetraisopropyl titanate solution into the titanium catalyst ligand solution, heat up to 75℃, keep warm for 5min, then cool down to 70℃, keep warm for 10min, then cool down to 65℃, add the compound solution of formula one and stir After 5 minutes, cool down to 58°C, keep warm for 20min, then add 2.322g N,N-diisopropylethylamine, cool down to 46°C, keep warm for 7min, then cool down to 35°C, keep warm for 5min; then cool down to -10°C, After stirring for ...

Embodiment 2

[0032] A kind of preparation method of dexla soprazole, this method comprises the steps: dissolve 2.84g tetraisopropyl titanate with 25mL organic solvent, be made into tetraisopropyl titanate solution, dissolve 8.02g titanium with 50mL organic solvent The catalyst ligand is made into a titanium catalyst ligand solution, wherein the titanium catalyst ligand is: L-(+)-diethyl tartrate, dissolves 3.53g of the compound of formula one with 25mL of organic solvent, and is made into a solution of the compound of formula one; The organic solvent is toluene; at 25°C, add tetraisopropyl titanate solution into the titanium catalyst ligand solution, heat up to 75°C, keep it warm for 5 minutes, then cool down to 70°C, keep it warm for 10 minutes, and then cool down to 65°C , add the compound solution of formula 1 and stir for 5 minutes, then cool down to 58°C, keep warm for 20min, then add 2.322g N,N-diisopropylethylamine, cool down to 46°C, keep warm for 7min, then lower the temperature to...

Embodiment 3

[0034] A kind of preparation method of dexla soprazole, this method comprises the steps: dissolve 2.84g tetraisopropyl titanate with 25mL organic solvent, be made into tetraisopropyl titanate solution, dissolve 8.02g titanium with 50mL organic solvent The catalyst ligand is made into a titanium catalyst ligand solution, wherein the titanium catalyst ligand is: (1S, 2S)-N-p-toluenesulfonic acid-1,2-diphenylethylenediamine, with 25mL of organic solvent Dissolve 3.53g of the compound of formula 1 to prepare a solution of compound of formula 1; the organic solvent is toluene; at 25°C, add tetraisopropyl titanate solution into the titanium catalyst ligand solution, heat up to 75°C, and keep it warm for 5 minutes , then lower the temperature to 70°C, keep it warm for 10 minutes, then lower the temperature to 65°C, add the compound solution of Formula 1 and stir for 5 minutes, then lower the temperature to 58°C, keep it warm for 20 minutes, then add 2.322g N,N-diisopropylethylamine, a...

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Abstract

The invention provides a preparation method of R-lansoprazole. According to the preparation method, a compound represented by formula 1 is taken as a raw material, a titanium catalyst ligand, an organic solvent, tetraisopropyl titanate, N, N-diisopropylethylaine, and an oxidizing agent are added, and R-lansoprazole is synthesized via catalytic oxidation. In the preparation method, the novel titanium catalyst ligand is adopted, so that the stability of a titanium catalyst compound is increased, the titanium catalyst compound can be filtered in solid, R-lansoprazole yield is increased, and compound ee value is increased obviously.

Description

technical field [0001] The invention belongs to the field of compound preparation, in particular to a preparation method of dexlansoprazole. Background technique [0002] Dexlansoprazole is a proton pump inhibitor, is the chiral monomer (R-configuration) of lansoprazole, and its specificity and non-competitive effect on H + / K + -ATPase, used in the treatment of peptic ulcer, chemical name: 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl] Sulfonyl]-1H benzimidazole, R-lansoprazole has more significant proton pump inhibitory effect than S-lansoprazole, and the action time is long. [0003] At present, the main method for the synthesis of dexlansoprazole is the asymmetric catalytic directional synthesis of dexlansoprazole, which mainly utilizes metals and their corresponding ligands to undergo an asymmetric catalytic oxidation reaction under the action of an oxidizing agent. The metal mainly used is titanium salt and the corresponding ligand L-tartaric acid derivat...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07B2200/07C07D401/12
Inventor 李剑峰周文
Owner 赛隆药业集团股份有限公司
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