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Method for compounding tedizolid phosphate

A technology of tedizolid phosphate and its synthesis method, which is applied in the field of pharmaceutical synthesis, can solve the problems of difficult access and high price of tedizolid, and achieve the effects of simple operation, environmental friendliness and low cost

Inactive Publication Date: 2015-12-02
成都维恒医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The existence of starting material tedizolid in this reaction is expensive and difficult to obtain

Method used

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  • Method for compounding tedizolid phosphate
  • Method for compounding tedizolid phosphate
  • Method for compounding tedizolid phosphate

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Experimental program
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Effect test

Embodiment 1

[0044] A method for synthesizing tedizolamide phosphate, comprising the following steps:

[0045] In the first step, the synthetic route of compound 4 is as follows:

[0046]

[0047] The specific method is: under the protection of nitrogen, add sodium hydrogen (NaH) (0.22g, 8.9mmol) and 40mL of dry tetrahydrofuran to a three-necked reaction flask, control the temperature at about 0°C, add compound 5 (2.50g, 7.4mmol), After stirring for 10 min, add dropwise 15mL solution of diethyl chlorophosphate (compound 6) (1.53g, 8.9mmol) in dry tetrahydrofuran. After the dripping is completed, stir at room temperature for 4h. TLC monitors the completion of the reaction. Add 100mL ice water to the system. It was extracted twice with 100 mL of ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to obtain 43.26 g of compound.

[0048] 1 H-NMR (400MHz, DMSO-d 6 ,δ / ppm): 7.81~7.77(t,1H), 7.58~7.54(dd,1H), 7.22~7.19(dd,1H), 4.83~4.72(m,1H), 4.25~4.1...

Embodiment 2

[0058] A method for synthesizing tedizolamide phosphate, comprising the following steps:

[0059] In the first step, the synthetic route of compound 4 is as follows:

[0060]

[0061] The specific method is: under the protection of nitrogen, add sodium hydrogen (0.22g, 8.9mmol) and dry tetrahydrofuran 40mL into a three-necked reaction flask, control the temperature at about 0℃, add compound 5 (2.14g, 7.4mmol), stir for 10min , Add dropwise a 30mL solution of dibenzyl chlorophosphate (compound 6) (2.63g, 8.9mmol) in dry tetrahydrofuran, after dropping, stir at room temperature for 4h, TLC monitors the completion of the reaction, and add 100mL of ice water to the system. 100 mL of ester was extracted twice, the organic phases were combined, dried with anhydrous sodium sulfate, and concentrated to obtain 43.73 g of compound.

[0062] 1 H-NMR(400MHz,DMSO-d 6 ,δ / ppm): 7.80~7.76(t,1H), 7.57~7.53(dd,1H), 7.34~7.28(m,10H), 7.21~7.18(dd,1H), 5.08~4.97(m,4H) , 4.84~4.73(m,1H), 4.26~4.14(m,2H...

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Abstract

The invention provides a method for compounding tedizolid phosphate, which uses a compound 5 as a staring material, and a novel antibacterial agent tedizolid phosphate is prepared through a reaction. The method for compounding the tedizolid phosphate is a novel industrialized compound selectivity mode, is simple and convenient in operation simultaneously, simple in after treatment, low in cost and environmentally friendly, can obtain high quality objective product, and is beneficial for industrial manufacture.

Description

Technical field [0001] The invention relates to the field of medical synthesis, and in particular to a method for synthesizing tedizolamide phosphate. Background technique [0002] Tedizolidphosphate, (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxymethyl Oxazolidin-2-one dihydrogen phosphate (Formula 1), which is applied by Cubist Pharmaceuticals for the treatment of Staphylococcus aureus (including methicillin-resistant strains and methicillin-sensitive strains) and various streptococci and fecal Acute bacterial skin and skin structure infections (ABSSSI) caused by Gram-positive bacteria such as Enterococcus; It was approved by the FDA on June 20, 2014, and its trade name is SIVEXTRO. [0003] Tedizolid phosphate belongs to the second generation of oxazolidinone antibiotics. The results of clinical trials show that the in vitro inhibitory activity of this drug against some bacteria is 2 to 8 times higher than that of linezolid. It is effective in gastro...

Claims

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Application Information

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IPC IPC(8): C07F9/6558
Inventor 杜全胜
Owner 成都维恒医药科技有限公司
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