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A kind of synthetic method of broad-spectrum antibiotic chloramphenicol

A synthesis method and technology of chloramphenicol, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of long synthesis route of chloramphenicol, production cost and increase of three wastes, etc., to solve the problems of three wastes, The effect of cost reduction

Active Publication Date: 2011-12-21
WUHAN WUYAO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] As can be seen from above, the synthetic route of chloramphenicol is long at present, because the theoretical highest yield of splitting only has 50%, makes production cost and three wastes increase, and aluminum isopropoxide reduction process also produces a large amount of three wastes that are difficult to handle, so looking for More economical synthetic methods are always a challenge

Method used

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  • A kind of synthetic method of broad-spectrum antibiotic chloramphenicol
  • A kind of synthetic method of broad-spectrum antibiotic chloramphenicol
  • A kind of synthetic method of broad-spectrum antibiotic chloramphenicol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1 (1R, 2R)-2-nitro-1-phenyl-1, the preparation of 3-propanediol

[0029] 0.9 g of Cu(OTf) 2 (0.25mmol), 1.2 grams of 2,6-bis[(S)-4-isopropyl-1-phenyl-4,5-dihydro-1H-2-imidazolyl]pyridine (2.6mmol) and 20 ml Add 1,4-dioxane into a 100 ml single-necked flask, replace the air inside with nitrogen to keep the nitrogen flow constant, stir with magnetic force for 2 hours, then cool with an ice bath, add 2.7 g of benzaldehyde (25 mmol), 22.8 g of 2 -Nitroethanol (250mmol) and N-methylmorpholine (0.27 milliliters, 2.5mmol), the reaction solution was stirred in an ice-bath cooling for 24 hours, after the thin-plate chromatography detected no raw material benzaldehyde spots, then evaporated under reduced pressure to remove volatile non-toxic solvent, the catalyst was removed by silica gel filtration, and the filtrate was concentrated to obtain 4.4 grams of product, the yield was 90%, and the e.e value was 93% as determined by HPLC. 1 H NMR (acetone-d 6 )δ: 3.46(ddd,...

Embodiment 2

[0030] The preparation of embodiment 2 (1R, 2R)-2-amino-1-phenyl-1,3-propanediol

[0031] Dissolve 5 g of (1R, 2R)-2-nitro-1-phenyl-1,3-propanediol (25 mmol) in 100 ml of methanol, add 0.1 g of 10% palladium-on-carbon catalyst, under hydrogen pressure 50Psi Hydrogenation reduction, no raw material spots detected by thin-plate chromatography, and the catalyst was removed by filtration. After the filtrate was concentrated, it was recrystallized with a 1:1 ethanol-ether mixed solvent to obtain 4.0 g of the product, with a yield of 94%, m.p.111-113 ° C, other data and literature to , Y.; Masaya, S.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. Concordance.

Embodiment 3

[0032] The preparation of embodiment 3 (1R, 2R)-2-dichloroacetamido-1-phenyl-1,3-propanediol

[0033] Add 4 grams of (1R, 2R)-2-amino-1-phenyl-1,3-propanediol (24mmol) and 40ml of methyl dichloroacetate (0.4mol) into a single-necked flask in turn, and stir at 100-110°C After 2 hours, thin plate chromatography detected no raw material spots, and then concentrated under reduced pressure. The solid was recrystallized from a mixed solvent of ethyl acetate and n-hexane to obtain 6.0 g of the product, with a yield of 93%, m.p.93-95°C.

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Abstract

The invention relates to a method for synthesizing broad-spectrum antibiotic chloramphenicol. In the method, benzaldehyde and 2-nitroethanol are used as raw materials and are synthesized in the presence of a chiral catalyst to obtain (1R, 2R)-2-nitro-1-phenyl-1,3-propylene glycol; the (1R, 2R)-2-nitro-1-phenyl-1,3-propylene glycol is subjected to hydrogenation reduction to obtain (1R, 2R)-2-amino-1-phenyl-1,3-propylene glycol; and the (1R, 2R)-2-amino-1-phenyl-1,3-propylene glycol is dichloroacetylated and nitrified to obtain the chloramphenicol. By using the method provided by the invention, chiral separation and aluminum isopropoxide reduction which are generally used in industry at present can be avoided; three wastes (waste water, waste gas and industrial residues) are reduced; and the method has the advantages of low-cost and readily available raw materials and reagents, less synthesis steps and high yield and is more suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of a compound, in particular to a synthesis method of a broad-spectrum antibiotic chloramphenicol. Background technique [0002] Chlorotoxin is a broad-spectrum antibiotic, mainly used for typhoid bacillus, Shigella, meningococcus, pneumococcus infection, and can also be used for rickettsial infection. Although it has many side effects such as inhibition of bone marrow hematopoietic function, causing coarse cells and thrombocytopenia or aplastic anemia, it is still the drug of choice for the treatment of typhoid fever. [0003] Chloramphenicol is white or slightly yellow-green needle-like, long flaky crystals or crystalline powder. Bitter. The melting point is 149-153°C. Soluble in organic solvents such as methanol, ethanol and acetone, slightly soluble in water. Specific rotation [α] D 25 =+18.5~+21.5° (absolute ethanol). [0004] There are many reports about the synthetic route of chloramphenicol, bu...

Claims

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Application Information

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IPC IPC(8): C07C233/18C07C231/12
Inventor 杨尚金冯珂朱毅谢国范潘季红
Owner WUHAN WUYAO PHARMA
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