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Intermediate for preparing linezolid and preparation method thereof

A technology for linezolid and intermediates, which is applied in the field of intermediates for preparing linezolid, can solve the problems of harsh reaction conditions, low product purity, large amount of solvent and the like, and achieves the use of less solvent amount, high product purity and easy product. Effect

Inactive Publication Date: 2012-10-17
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The technologies disclosed in the above documents and patents have the disadvantages of using a large amount of solvent, using expensive reagents such as n-butyllithium and diisopropylamide lithium, low reaction yield, harsh reaction conditions, using dangerous goods such as sodium azide, and the product is not easy Purification, defects such as low product purity

Method used

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  • Intermediate for preparing linezolid and preparation method thereof
  • Intermediate for preparing linezolid and preparation method thereof
  • Intermediate for preparing linezolid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of (S)-1-chloro-3-[(3-nitro-E-benzylidene)-amino]-propan-2-ol

[0040]

[0041] Mix m-nitrobenzaldehyde (151g, 1mol), MTBE400ml, ammonia water 27.2g, (S)-epichlorohydrin (93g, 1mol) into the reaction flask, react at room temperature for 20h, separate layers, discard the water layer, and organic The layer was evaporated to dryness to obtain a white solid, which was beaten and washed with n-hexane to obtain the product.

[0042] m / z: 242.05

[0043] Elemental analysis: C, 49.50; H, 4.57; Cl, ​​14.61; N, 11.54; O, 19.78.

[0044] 1 H NMR: 63.5(d, 1H), 3.58(m, 1H), 3.65(d, 2H), 3.83(d, 2H), 7.78(m, 1H), 8.15(m, 1H), 8.22(m, 1H ), 8.52(s, 1H).

Embodiment 2

[0046] Preparation of (S)-1-chloro-3-[(4-hydroxy-E-benzylidene)-amino]-propan-2-ol

[0047]

[0048] 4-Hydroxybenzaldehyde (122g, 1mol), MTBE300ml, ammonia water 27.2g, (S)-epichlorohydrin (93g, 1mol) were mixed into the reaction flask, after 20h reaction at room temperature, the layers were separated, the aqueous layer was discarded, and the organic The layer was evaporated to dryness to obtain a white solid, which was pulped and washed with petroleum ether to obtain the product.

[0049] m / z: 213.06

[0050] Elemental analysis: C, 56.21; H, 5.66; Cl, ​​16.59; N, 6.56; O, 14.98

[0051] 1 H NMR: δ3.61(d, 1H), 3.63(m, 1H), 3.715(d, 2H), 3.85(d, 2H), 5.53(s, 1H), 6.85(m, 1H), 6.85(m , 1H), 7.81(m, 1H), 7.81(m, 1H), 8.76(m, 1H).

Embodiment 3

[0053] Preparation of (S)-1-chloro-3-[(2-nitro-E-benzylidene)-amino]-propan-2-ol

[0054]

[0055] Mix 2-nitrobenzaldehyde (151g, 1mol), MTBE400ml, ammonia water 27.2g, (S)-epichlorohydrin (93g, 1mol) into the reaction flask, react at room temperature for 20h, separate layers, discard the water layer, The organic layer was evaporated to dryness to obtain a white solid, which was pulped and washed with n-hexane to obtain the product.

[0056] m / z: 242.05

[0057] Elemental analysis: C, 49.50; H, 4.57; Cl, ​​14.61; N, 11.54; O, 19.78

[0058] 1 H NMR: δ3.51(d, 1H), 3.58(m, 1H), 3.67(d, 2H), 3.85(d, 2H), 7.59(m, 1H), 7.91(m, 1H), 7.98(m , 1H), 8.09 (m, 1H), 8.76 (s, 1H).

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Abstract

The invention discloses an intermediate for preparing linezolid and a preparation method thereof. The method for preparing linezolid by the use of the intermediate provided by the invention has advantages as follows: the volume of a solvent used is small; the product is easy to purify, and the purity of the product is high, and is an environmental protection method. The general chemical formula of the intermediate is as shown in the formula (I).

Description

technical field [0001] The present invention relates to intermediates useful in the preparation of linezolid. Background technique [0002] Antimicrobial resistance is a global clinical and public health problem. A large number of clinical resistance problems have emerged at an alarming rate in recent years and will increase significantly in the near future. In the case of a sharp increase in the spread of bacteria, drug resistance has become an important issue that seriously endangers society and public health. Multidrug resistance is a growing problem and, therefore, the development of structurally novel antimicrobials with novel mechanisms of action is increasingly important in the treatment of bacterial infections. [0003] Among such structurally novel antibacterial drugs, linezolid is an antibacterial drug active against a large number of pathogenic microorganisms. The structural formula of linezolid is disclosed in US Patent No. 5,688,792, as follows: [0004] ...

Claims

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Application Information

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IPC IPC(8): C07C251/24C07C249/02C07D263/20
Inventor 李建其金华王伟
Owner SHANGHAI INST OF PHARMA IND
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