Preparation method of 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone

A technology of hydroxymethyloxazolidine and phenyl, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of low utilization rate of carbon atoms, failure to meet the development trend, high production cost, etc., so as to improve the safety production factor and the price of raw materials Inexpensive, less environmental pollution effect

Active Publication Date: 2012-01-18
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The utilization rate of carbon atoms is not high, which means that organic by-products are produced in the reaction process. Therefore, it means that resources are wasted and environmental pollution is caused. development trend

Method used

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  • Preparation method of 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone
  • Preparation method of 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone
  • Preparation method of 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056]

[0057] Add 29.4g (0.15mol) of 3-fluoro-4-(4-morpholinyl)aniline and (S)-3-chloro-1,2-propanediol into a 500ml four-necked flask equipped with stirring, condenser and thermometer 11.05g (0.1mol), 4.4g (0.11mol) of sodium hydroxide and 200ml of ethanol, stirred and heated to reflux for 12hrs.

[0058] The solvent was removed under reduced pressure, 200 ml of water was added, and stirred for 1 hr. After suction filtration, the aqueous solution of compound (2) was obtained, which can be directly used in the next step of cyclization reaction. After quantitative analysis, it contained 23.06g of (R)-(+)-3-(3-fluoro-4-morpholineanilino)-1,2-propanediol. Yield 85.4%.

[0059]

[0060] Stirring is equipped with in 1000ml, dropping funnel and thermometer add about 350ml (0.0854mol) of aqueous solution containing 23.06g compound (2) in example 1, 100ml dichloroethane. Under ice-salt bath cooling, control the liquid temperature at 0-5°C, and slowly add 120ml (0.11mol) of ...

Embodiment 2

[0067] Except that the amount of 3-fluoro-4-(4-morpholino)aniline is 19.6 g (0.1 mol), the others are the same as in Example 1. The aqueous solution of compound (R)-(+)-3-(3-fluoro-4-morpholineanilino)-1,2-propanediol was obtained, which can be directly used in the next step of cyclization reaction. After quantitative analysis, it contained 17.55g of (R)-(+)-3-(3-fluoro-4-morpholineanilino)-1,2-propanediol. The yield is 65%.

Embodiment 3

[0069] Except that ethanol is replaced with isopropanol, all the other are the same as embodiment one. The aqueous solution of compound (R)-(+)-3-(3-fluoro-4-morpholineanilino)-1,2-propanediol was obtained, which can be directly used in the next step of cyclization reaction. After quantitative analysis, it contained 19.04g of (R)-(+)-3-(3-fluoro-4-morpholineanilino)-1,2-propanediol. Yield 70.5%.

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Abstract

The invention discloses a preparation method of 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone. The preparation method comprises the following steps: carrying out condensation reaction on substituted aniline which is used as a starting material and 3-sustituted-1,2-propanediol so as to synthesize an intermediate (R)-(+)-3-substituted phenylamino-1,2-propanediol; and preparing 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone through two-step reaction, wherein the obtained product 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone is an important intermediate used for commercially producing oxazolidinone antibacterial agents. The method for preparing 3-substituted phenyl-5-hydroxymethyloxazolidine-2-ketone through two-step reaction has the characteristics of less steps, cheap and available raw materials, mild reaction conditions and the like, and is simple to operate; and by using the method in the invention, production efficiency is improved, production energy consumption is reduced, safe production coefficient is improved, production cost is reduced, environment pollution is reduced, thus the method in the invention is an environmentally-friendly low-carbon green synthesis method.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of a key intermediate 3-substituted phenyl-5-hydroxymethyl oxazolidin-2-one for the preparation of an oxazolidinone antibacterial agent. Background technique [0002] Oxazolidinone antibacterial agents are a new class of antibacterial agents whose mechanism of action is different from other antibacterial agents. 3-substituted phenyl-5-hydroxymethyl oxazolidin-2-one is a key intermediate necessary for the synthesis of this class of drugs (see: Steven JB, et al. J Med Chem, 1996, 39 (3): 673-679; Meng Qingguo, Wang Qi, Liu Jun, Acta Pharmaceutica Sinica, 2003, 38 (10): 754-759; Barbachyn, MR et al., WO9507271; Barbachyn, MR et al., ZL94193313.x; Perlman, BA et al., ZL97193658 .7; Perlman, BA et al., ZL01133003.1; Xu Guangyu et al., ZL200410017127.0; Barbachyn, MR et al., ZL200510048548.4). [0003] In the prior art, most of the preparat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/24
CPCY02P20/55
Inventor 沈建伟吴和明朱崇泉
Owner SUZHOU JINGYE MEDICINE & CHEM
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