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boc-(r)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid condensation impurity and preparation method thereof

A technology of trifluorophenyl and amino groups, applied in the field of organic synthesis medicinal chemistry, can solve the problems of unfavorable industrial production, high cost, low general yield and the like, and achieve the effects of easy control, moderate reaction conditions, simple and efficient operation

Active Publication Date: 2021-07-02
ZHEJIANG YONGTAI TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the refining method of the final product removes impurity A, the general yield is low, and the cost is high, which is not conducive to industrial production

Method used

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  • boc-(r)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid condensation impurity and preparation method thereof
  • boc-(r)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid condensation impurity and preparation method thereof
  • boc-(r)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid condensation impurity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Example 1 Preparation of BOC- (R) -3-amino-4- (2,4,5-trifluorophenyl) butyric acid condensation impurities

[0088] 500 ml of four-mouth flask was input to 10 g (0.03 mol), (0.03 mol), (R) -3-amino-4- (2) (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) 4,5-trifluorophenyl) butyric acid 8 g (0.0297 mol), HOBT 5g (0.036 mol), EDC-HCl 7g (0.036 mol), and 90 g of acetonitrile, the solid was dispersed uniform. Triethylamine 4g (0.04 mol) was added dropwise, and the temperature was controlled from 20 to 30 ° C, and the insulation reaction was controlled until the end point. The acetonitrile was recovered under reduced pressure to give a solid crude material. The concentrate was purified by silica gel column (dichloromethane: ethyl acetate = 8: 1) Collecting eluent containing impurities, concentrated to dryness to give a white solid 11.5 g, purity of about 99%, yield of about 70%.

[0089] The solid obtained by preparing in Example 1 was analyze...

Embodiment 2

[0097] Example 2 Preparation of BOC- (R) -3-amino-4- (2,4,5-trifluorophenyl) butyric acid condensation impurities

[0098] 500 ml of four-mouth flask was input to 10 g (0.03 mol), (0.03 mol), (R) -3-amino-4- (2) (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) 4,5-trifluorophenyl) butyric acid 8 g (0.0297 mol), HOBT 5g (0.036 mol), EDC-HCl 7g (0.036 mol), and 90 g of acetonitrile, the solid was dispersed uniform. 2.4 g (0.04 mol) was added dropwise, and the temperature was controlled from 20 to 30 ° C, and the insulation reaction was controlled until the end point. The acetonitrile was recovered under reduced pressure to give a solid crude material. The concentrate was purified by silica gel column (dichloromethane: ethyl acetate = 8: 1) Collect eluent containing impurities, concentrated to dryness to give a white solid. The solid was 10.68 g, which was about 99% purity, and the yield was about 65%.

Embodiment 3

[0099] Example 3 BOC- (R) -3-amino-4- (2,4,5-trifluorophenyl) butyric acid condensation impurities

[0100]500 ml of four-mouth flask was input to 10 g (0.03 mol), (0.03 mol), (R) -3-amino-4- (2) (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) -3-amino-4- (2) 4,5-trifluorophenyl) butyric acid 8 g (0.0297 mol), HOBT 5g (0.036 mol), EDC-HCl 7g (0.036 mol), and 90 g of acetonitrile, the solid was dispersed uniform. Pyridine 3.16 g (0.04 mol) was added dropwise, the temperature was 20-30 ° C, and the insulation reaction was controlled until the end point. The acetonitrile was recovered under reduced pressure to give a solid crude material. The concentrate was purified by silica gel column (dichloromethane: ethyl acetate = 8: 1) Collect eluent containing impurities, concentrated to dryness to give a white solid. The solid was 9.86 g, the purity was about 99%, and the yield was about 60%.

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Abstract

The invention provides an important intermediate of sitagliptin phosphate, BOC-(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid condensation impurity, a preparation method and application thereof. The invention provides BOC-(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid condensation impurities and a preparation method thereof, which is of great significance to the industrial production of subsequent raw materials.

Description

Technical field [0001] The present invention relates to the field of organic synthetic pharmaceutical chemistry, and more particularly to a phosphate, a phosphate-3-amino-4- (2,4,5-trifluorophenyl) butyric acid Temurizing and preparation method thereof. Furthermore, the invention also relates to a method of controlling the quality of Western littin by controlling the impurity content. Background technique [0002] Sitagliptin Phosphate is developed in US Merck, in October 2006, through FDA approved the first secondary peptidin-based (DPP-IV) inhibitor, the National Food and Drug Administration has officially approved The merchandise is available in Januvia. [0003] Sitagliptin phosphate is as follows: [0004] [0005] BOC- (R) -3-amino-4- (2,4,5-trifluorophenyl) butyric acid is a key intermediate of a phosphate. The structure is as follows: [0006] [0007] Western phosphate is mainly used in the treatment of type II diabetes. It is singular or combined with metformin, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C269/06C07C271/20C07D487/04
Inventor 张峰程旭阳覃晓
Owner ZHEJIANG YONGTAI TECH CO LTD
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