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Method for synthetizing Tegoprazan chiral alcohol

A technology of chiral reagents and benzopyrans, which is applied in the field of synthesizing chiral fragments of raw materials, can solve the problems of low chiral purity of products, low yield, and expensive chiral reagents, and achieve easy procurement, simple synthesis methods, The effect of simple process operation

Active Publication Date: 2019-02-12
WISDOM PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented synthetic methods involve simpler steps than existing ones but they still require expensive chemicals that can be difficult or dangerous to handle at large scales. These new techniques have improved efficiency over older ways while also being more effective on producing certain types of compounds like 5, 7 - difluorochloro 3 , 4- dihydronaphthalene.

Problems solved by technology

This patented technical problem addressed in this patent describes how to efficiently manufacture high quality crystal forms called Tegprotuzina or Pertiaryotriptinum Acquisition II®(PTZOPYRIX™) containing an antihypertensive agent like etodilastonabilex or Prochloro Therapeutic Agrosis Disorders Group B1a metabolism therapy. However, current methods have limitations due to their low efficiency and potential side effects caused by impurities present during production processes. Therefore, these techniques must overcome before being commercially available.

Method used

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  • Method for synthetizing Tegoprazan chiral alcohol
  • Method for synthetizing Tegoprazan chiral alcohol
  • Method for synthetizing Tegoprazan chiral alcohol

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: Preparation of (S)-5,7-difluoro-4H-benzopyran-4-ol

[0025] Add anhydrous THF (400mL) and (S)-tetrahydro-1-methyl-,3,3-diphenyl-1H,3H-pyrrolo[1,2-c to a 3L reaction flask under nitrogen protection ][1,3,2]Oxazoborin in toluene (1M in Toluene, 55 mL, 55 mmol). After the addition, the system was cooled to 0±2°C in an ice-salt bath, then borane dimethyl sulfide complex (1M in THF, 575mL, 0.575mol) was added to the system, the system was stirred at 0±2°C for 10min, and then 5, 7-difluoro-4H-benzopyran-4-one (100g, 0.549mol) in THF (500mL) solution, the reaction temperature of the system was maintained at 0±2°C during the addition process, and the system reacted to TLC to track the starting material after the addition was completed 5,7-Difluoro-4H-benzopyran-4-one disappeared. After the reaction was completed, the system was quenched by adding MeOH (200 mL), and the system was naturally warmed to room temperature and stirred vigorously for 1 hour. The organic s...

Embodiment 2

[0026] Example 2: Preparation of (S)-5,7-difluoro-4H-benzopyran-4-ol

[0027] Add anhydrous THF (80mL) and (S)-tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1, 3,2] Oxazoborin in toluene (1M in Toluene, 11.0 mL, 11.0 mmol). After the addition, the temperature of the system was cooled to 0±2° C. in an ice-salt bath, and then borane dimethyl sulfide complex (1M inTHF, 121 mL, 121 mmol) was added to the system. After the system was stirred at 0±2°C for 10 minutes, a solution of 5,7-difluoro-4H-chromen-4-one (20.0g, 109.8mmol) in THF (100mL) was added, and the reaction temperature of the system was maintained at 0±2°C during the addition process After the addition was complete, the system reacted until the material 5,7-difluoro-4H-benzopyran-4-one disappeared by TLC tracking. After the reaction was completed, the system was quenched by adding MeOH (50 mL), and the system was naturally warmed to room temperature and stirred vigorously for 1 hour. The organic solvent of the sys...

Embodiment 3

[0028] Example 3: Preparation of (S)-5,7-difluoro-3,4-dihydro-2H-chromen-4-ol

[0029]Add (S)-5,7-difluoro-4H-benzopyran-4-ol (5.0g, 27.15mmol) and ethanol (100mL) to the reaction flask, stir the system, then add 5% Pd under nitrogen protection / C (water content 65%, 5.8g). After the addition was complete, the system was replaced with nitrogen three times, and then hydrogenated at room temperature and pressure until the disappearance of the reaction raw materials tracked by HPLC. Filtrate, remove the organic solvent under high vacuum, and purify the residue by column chromatography (n-heptane / EA=5:1) to obtain (S)-5,7-difluoro-3,4-dihydro-2H-chromene -4-ol (4.65 g, 92%).

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Abstract

The invention relates to a method for synthetizing Tegoprazan chiral alcohol, in particular to a preparation method of (S)-5,7-difluoro-3,4-dihydro-2H-chromene-4-alcohol. The method is characterized in that 5,7-difluoro-4H-benzopyran-4-ketone is used as a starting material; through chiral reagents, ketone carbonyl groups are subjected to asymmetric reduction and subsequent conventional hydrogenation reaction; the preparation of the (S)-5,7-difluoro-3,4-dihydro-2H-chromene-4-alcohol is realized.

Description

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Claims

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Application Information

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Owner WISDOM PHARM CO LTD
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