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Method for preparing broad-spectrum antibiotic chloramphenicol

A technology of chloramphenicol and structural formula, applied in the field of compound preparation, can solve the problems of long synthesis route of chloramphenicol, production cost and increase of three wastes, etc., and achieve the effect of solving the three wastes and reducing costs

Active Publication Date: 2014-06-04
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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  • Method for preparing broad-spectrum antibiotic chloramphenicol
  • Method for preparing broad-spectrum antibiotic chloramphenicol
  • Method for preparing 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] Embodiment 3 (1R, 2R)-2-amino-1-p-nitrophenyl-1, the preparation of 3-propanediol

[0033] Slowly add 4 grams of (1R,2R)-2-amino-1-phenyl-1,3-propanediol (24mmol) into 15ml of concentrated sulfuric acid in batches, cool to -2~0°C, and then add 15ml Nitric acid, stirred at the above temperature for 5 hours, no raw material spots were detected by thin-plate chromatography, and the reaction solution was poured into 500 grams of ice, then carefully neutralized with 30% aqueous sodium hydroxide solution, extracted three times with dichloromethane, and combined to extract liquid, concentrated after drying, and recrystallized with a small amount of water to obtain 2.8 g of the product, with a yield of 55%, m.p.141-143°C. The NMR spectrum is consistent with the literature Hazra, B.G., Pore, V.S., Maybhate, S.P., Natekar, M.V. and Rao, A.S., Synfh.Commiin., 1989, 19, 1763.

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Abstract

The invention relates to a method for preparing broad-spectrum antibiotic chloramphenicol. In the method, benzaldehyde and 2-nitroethyl alcohol are taken as raw materials; (1R, 2R)-2-nitro-1-phenyl-1,3-propanediol is obtained through synthesizing the raw materials under the presence of a chiral catalyst; (1R, 2R)-2-amino-1-phenyl-1,3-propanediol is obtained through hydrogenization to reduce; and the chloramphenicol is obtained through carrying out nitrification and dichloro-acetylation on the intermediate. With the adoption of the method provided by the invention, the chiral separation and the reduction of aluminum isopropoxide which are commonly used in industry nowadays can be avoided, the three wastes are reduced, the raw materials and reagents are cheap and easy to get, the synthetic steps are little, the yield is high, and thus, the method is more suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/18C07C231/02
Inventor 杨尚金冯珂潘季红谢国范朱毅
Owner WUHAN WUYAO PHARMA
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