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Preparation method of tedizolid phosphate

A technology for tedizolid phosphate and a compound, which is applied in the field of chemical drug synthesis, can solve problems such as being unsuitable for industrial production, harsh synthesis conditions, harsh reaction conditions, etc., and achieves the effects of avoiding alkylating reagents, short synthesis steps, and easy purification

Inactive Publication Date: 2016-03-23
NANJING CORE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The preparation method disclosed in this patent has a total of 6 steps of reaction. The process undergoes steps such as substitution, condensation, cyclization, resolution, and esterification to prepare the target product. In the synthesis process of this method, there is a step in which the synthesis conditions are very harsh. React at ℃, and use toxic ICH 3 As an alkylating agent, the method has long reaction steps, harsh reaction conditions, low overall yield, high production cost, and is not suitable for industrial production.

Method used

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  • Preparation method of tedizolid phosphate

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Embodiment 1

[0032] (1) Compound 3-[3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridyl]phenyl]-5-(hydroxymethyl Synthesis of base)-2-oxazolidinone

[0033] In a 3000mL four-neck round-bottomed flask, install mechanical stirring, reflux condenser, thermometer, and add 1500mL tetrahydrofuran and 100g (5R)-3-(4-bromo-3-fluorophenyl) to the round-bottomed flask under nitrogen protection. -5-hydroxymethyloxazolidin-2-one, 105g2-(2-methyl-2H-tetrazol-5-yl)pyridine-5-boronic acid pinacol ester, 28g tetrakis(triphenylphosphine)palladium , start stirring until the solid dissolves, add 140 g of prepared potassium carbonate solution dissolved in a small amount of water, heat up to reflux, stir and react for 12 hours, and cool down to room temperature. Suction filtration, the filter cake was washed with water and then washed with acetone. The filter cake was vacuum dried at 45°C for 48 hours to obtain 80.2 g of product. Yield: 62.8%.

[0034] (2) Synthesis of compound tedizolid phosphate crude pr...

Embodiment 2

[0048] (1) Compound 3-[3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridyl]phenyl]-5-(hydroxymethyl Synthesis of base)-2-oxazolidinone

[0049] In a 3000mL four-neck round bottom flask, install mechanical stirring, reflux condenser, thermometer, and add 1500mL toluene and 100g (5R)-3-(4-bromo-3-fluorophenyl) to the round-bottom flask under argon protection )-5-hydroxymethyloxazolidin-2-one, 105g2-(2-methyl-2H-tetrazol-5-yl)pyridine-5-boronic acid pinacol ester, 28g dichlorobis(triphenylphosphine ) palladium, start stirring until the solid dissolves, add a small amount of water-soluble potassium carbonate solution prepared in 140g, heat up to reflux, stir and react for 12 hours, and cool to room temperature. After suction filtration, the filter cake was washed with water and then washed with a mixture of methanol and ethanol. The filter cake was vacuum dried at 45°C for 48 hours to obtain 81.3 g of product. Yield: 63.7%.

[0050] (2) Synthesis of compound tedizolid phosphat...

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Abstract

The invention belongs to the technical field of synthesis of chemical medicines and particularly relates to a preparation method of tedizolid phosphate. (5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one and 2-(2-methyl-2H-tetrazolyl-5-yl) pyridine-5-boronic acid pinacol ester are taken as raw materials, and (R)-3-(4-(2-(2-methyl tetrazole-5-yl) pyridine-5-yl)-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-ketone phosphate is prepared with a four-step method. The method has a mild process condition, aftertreatment is simple, the purity is high, the reaction cost is low, and industrial production is easy to realize.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and in particular relates to a preparation method of tedizolid phosphate. Background technique [0002] Tedizolidphosphate (Tedizolidphosphate), the chemical name is (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5 -Hydroxymethyloxazolidin-2-one phosphate, the structural formula is as follows: [0003] [0004] Tedizolid Phosphate is produced by Cubistpharmsinc and is used to treat adult patients with skin infections. It is a second-generation oxazolidinone antibiotic and is a protein synthesis inhibitor that inhibits bacterial protein synthesis. It is mainly used to treat acute bacterial skin and skin tissue infections caused by certain sensitive bacteria, such as Staphylococcus aureus (including methicillin-resistant strains and methicillin-sensitive strains), various streptococci and Enterococcus faecalis. [0005] The synthetic method of tedizolid phosph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558
CPCC07F9/65583
Inventor 王雪根何凌云余洋李晓静
Owner NANJING CORE TECH CO LTD
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