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Environment-friendly synthesis method of linezolid and intermediate thereof

A technology of linezolid and body formula, which is applied in the field of preparation of linezolid and its intermediates, can solve the problems of low reaction yield, large environmental pollution, and long steps in the synthesis route, and achieve simple process operation, high reaction yield, The effect of high product purity

Active Publication Date: 2018-10-26
上海圣赢生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above synthetic routes all adopt chiral epichlorohydrin or chiral epoxypropylene derivatives to introduce chiral neutrality, the synthetic route steps are long, and reaction conditions such as deep cooling are required in the reaction process, the reaction yield is low, and the cost is high. Great pollution to the environment

Method used

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  • Environment-friendly synthesis method of linezolid and intermediate thereof
  • Environment-friendly synthesis method of linezolid and intermediate thereof
  • Environment-friendly synthesis method of linezolid and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] Add 105 g of L-serine and 500 ml of DMF to the reaction flask, cool in an ice-water bath to 0°C, add 80 g of imidazole, slowly add 157 g of TBSCl in batches, and then raise to room temperature and stir for 16 hours. Add 500ml of water to quench the reaction, concentrate under reduced pressure to recover most of the solvent, add 500ml of water and 500ml of dichloromethane for extraction, combine the organic phases, dry over anhydrous sodium sulfate, and concentrate to obtain 2210g of the intermediate, with a yield of 95.9%, MS: 220.13[ M+H + ].

Embodiment 2

[0031]

[0032] Add 2219g of the intermediate, 1L of tetrahydrofuran, and 100mL of methanol into the three-necked flask, cool in an ice-salt bath to about 0-5°C, add 40g of sodium borohydride, and add 100ml of tetrahydrofuran solution of 127g of iodine dropwise after the addition, and raise the temperature of the reaction system to Return to reflux, and continue to stir the reaction for 2 hours. After the reaction of the raw materials is detected by TLC, 500ml of saturated ammonium chloride aqueous solution is used to quench the reaction, distilled under reduced pressure, the residue is extracted with ethyl acetate (300mL×2), and the organic phase is sequentially washed with saturated carbonic acid Wash with sodium hydrogen aqueous solution and brine, dry over anhydrous sodium sulfate and concentrate, intermediate 3200g, yield 97.5%, MS: 206.37[M+H + ].

Embodiment 3

[0034]

[0035] Add 3205g of the above-mentioned intermediate and 1L of dichloromethane into the reaction flask, cool to 0°C and add 390g of triphenylphosphine and 267g of NBS, after the addition is completed, raise the temperature to room temperature and stir for 4 hours, add 1L of water to quench the reaction, and let stand to separate the liquid. The organic phase was washed with 500 mL of saturated brine, and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain intermediate 4. The crude product of intermediate 4 was directly used in the next reaction without purification.

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Abstract

The invention relates to a more environment-friendly synthesis method of linezolid and a key intermediate thereof. The more environment-friendly synthesis method is characterized in that the key intermediate of linezolid is prepared through the steps of hydroxyl protection, carboxyl reduction, hydroxyl halogenation, ring closing, halogenation after hydroxyl deprotection, ring opening and the likeby taking a natural chiral product L-serine as an initial raw material. According to the more environment-friendly synthesis method provided by the invention, a chiral center is introduced by adoptingthe natural chiral product, the reaction yield is high, the technological operation is simple, the product purity is high, and the synthesis method is more environment-friendly and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing an oxazolidinone antibacterial agent, in particular to a method for preparing linezolid and an intermediate thereof. Background technique [0002] Linezolid is a synthetic oxazolidinone antibiotic with novel structure, unique mechanism of action and no cross-resistance. It is used to treat infections caused by Gram-positive (G+) cocci, including those caused by methicillin-resistant Suspected or confirmed hospital-acquired pneumonia (HAP), community-acquired pneumonia (CAP), complicated skin or skin and soft tissue infection (SSTI) caused by Staphylococcus aureus (MRSA), and vancomycin-resistant enterococcus (VRE) infection. [0003] The document "Chemical and Biological Engineering" vol.30.NO.1, 57-59 (2013) discloses a method for preparing linezolid, and its synthetic route is as follows: [0004] [0005] The document "Org.process Res Dev" 7(4):533-546 discloses a method for preparing linezolid. I...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C215/08C07D263/20
CPCC07C213/00C07C215/08C07D203/08C07D263/20C07F7/10C07B2200/07Y02P20/55
Inventor 王北朝崔兴周李广侠
Owner 上海圣赢生物科技有限公司
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