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A kind of preparation method of S-N-glycidyl phthalimide

A technology for the reaction of glycerol phthalimide and phthalimide, which is applied in the directions of organic chemistry, organic chemistry, etc., can solve the problems of difficult industrialization, harsh reaction conditions, and high industrialization costs, and achieves a reduction in Production costs, shortened response times, avoids the effects of special requirements

Active Publication Date: 2020-02-21
ZHEJIANG YONGTAI TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0027] Use a large amount of phase-transfer catalysts (close to 50% of starting material) in this operational route; TBAB is difficult to handle cleanly and seriously affects product quality in reaction; This operational route two-step total yield only has 58%, industrialization cost is high
[0028] In summary, the current process for synthesizing S-N-glycidyl phthalimide generally has problems such as harsh reaction conditions, low yield, high cost, poor quality, and difficult industrialization.

Method used

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  • A kind of preparation method of S-N-glycidyl phthalimide
  • A kind of preparation method of S-N-glycidyl phthalimide
  • A kind of preparation method of S-N-glycidyl phthalimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: Preparation of 2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione (Compound I)

[0058]

[0059] Put phthalimide (200.0 g 1.36 mol), 2.0 g of Amberlite FPA90OH anion resin, 2.0 g of TMBAC, 600 g of isopropanol, and 46.0 g of S-epichlorohydrin into a four-necked flask, and stir. Control the internal temperature at 15-25°C and keep it warm for 12 hours, take samples and control it until the residual phthalimide in the reaction solution is ≤1.0%, and the reaction is over. Concentrate to remove isopropanol, add 800g of toluene to dissolve and filter, and recover the resin for use; the filtrate is washed with water 2×200g, concentrated, and crystallized by adding 900g of n-heptane to obtain 300g of compound I (yield 92.1%)

Embodiment 2

[0060] Example 2: Preparation of 2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione (Compound I)

[0061]

[0062] Put phthalimide (200.0g 1.36mol), Amberlite FPA90OH anion resin (recovered from Example 1) 2.0g, TMBAC 2.0g, isopropanol 600g, S-epichlorohydrin 46.0g into a four-necked bottle medium, stir. Control the internal temperature at 15-25°C and keep it warm for 12 hours, take samples and control it until the residual phthalimide in the reaction solution is ≤1.0%, and the reaction is over. Concentrate to remove isopropanol, add 800g of toluene to dissolve and filter, and recover the resin for use; the filtrate is washed with 2×200g of water, concentrated, and crystallized by adding 900g of n-heptane to obtain 298.0g of compound I (yield 91.5%).

Embodiment 3

[0063] Example 3: Preparation of 2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione (Compound I)

[0064]

[0065] Put phthalimide (200.0g 1.36mol), Amberlite FPA90OH anion resin (recovered from Example 2) 2.0g, TMBAC 2.0g, isopropanol 600g, S-epichlorohydrin 46.0g into a four-necked bottle medium, stir. Control the internal temperature at 15-25°C and keep it warm for 12 hours, take samples and control it until the residual phthalimide in the reaction solution is ≤1.0%, and the reaction is over. Concentrate to remove isopropanol, add 800g of toluene to dissolve and filter, and recover the resin for use; the filtrate is washed with 2×200g of water, concentrated, and crystallized by adding 900g of n-heptane to obtain 297.0g of compound I (91.2% yield).

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Abstract

The invention relates to a preparation method of S-N-glycidol phthalimide. According to the method, recyclable anion exchange resin is used for catalyzing reaction in the preparation process of the S-N-glycidol phthalimide, so that the production cost is reduced; the emission requirements are reduced; the problem that a phase transfer catalyst is difficultly removed and influences the quality of aproduct is solved; the reaction time is further reduced; the special requirements on equipment caused by application of potassium tert-butoxide are avoided; the production cost is reduced; the preparation method is suitable for industrial production.

Description

technical field [0001] The present invention relates to the field of organic synthetic medicinal chemistry, more specifically, to a preparation method of S-N-glycidyl phthalimide Background technique [0002] S-N-glycidyl phthalimide is an important pharmaceutical intermediate for the preparation of oxazolidinone compounds such as the new antibiotic linezolid and the new oral anticoagulant drug rivaroxaban. The general synthetic route of linezolid and rivaroxaban is as follows: [0003] [0004] Rivaroxaban and linezolid are clinically safe drugs; the market situation is relatively good. The chiral purity of S-N-glycidylphthalimide plays a key role in the quality of these two drugs; therefore, the preparation of S-N-glycidylphthalimide with high chiral purity is increasingly The attention of engineers; the reported synthesis routes are mainly: [0005] Synthetic route 1 [0006] Tetrahedron 1996 (7) 1641-1648 reported that biphenyl dicarboximide and R-epichlorohydrin ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48C07D405/06
CPCC07B2200/07C07D209/48C07D405/06
Inventor 王学进甘立新周国斌徐旭炳杨家乐张冲
Owner ZHEJIANG YONGTAI TECH CO LTD
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