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Method for preparing florfenicol intermediate salt

A technology of florfenicol and intermediates, which is applied in the field of preparation of florfenicol intermediate salts, can solve the problems of large sewage discharge, high cost, difficult recovery of glycerin, etc., and achieves convenient operation, good product quality and excellent reaction conditions mild effect

Active Publication Date: 2014-09-03
XINCHANG HEBAO BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] After the reduction reaction, use glycerol to quench the reduction reaction, and use glycerol to deboron and use glycerol as a solvent for the next reaction. This process has disadvantages such as difficult recovery of glycerin, high cost, and large sewage discharge.

Method used

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  • Method for preparing florfenicol intermediate salt
  • Method for preparing florfenicol intermediate salt
  • Method for preparing florfenicol intermediate salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In the three-necked flask, add 300g (9.36mol) methanol, 50g (0.17mol) D-threo-p-methylsulfonylphenylserine ethyl ester, raise the temperature to 35°C, add 13g (0.24mol) potassium borohydride, and keep warm for 5 hours , then add 50g (0.41mol) concentrated hydrochloric acid to adjust the pH to 3-3.5, keep warm at 75-80°C for 2-2.5 hours, distill off methanol and boron ester, adjust the pH of the residue to 7-7.5 with potassium hydroxide, spray dry, The hydrochloride product of the reduced product of the formula was 49.03 grams, the yield was 100%, the fixed nitrogen content was 4.90%, and the mp (melting point) was 152-154°C.

Embodiment 2

[0024] In the three-necked flask, add 300g (9.36mol) methanol, 50g (0.17mol) D-threo-p-methylsulfonylphenylserine ethyl ester, raise the temperature to 35°C, add 13g (0.24mol) potassium borohydride, and keep warm for 5 hours , then add 30g (0.311mol) of sulfuric acid to adjust the pH to 1-1.5, keep it warm at 50-55°C for 1-1.5 hours, evaporate methanol and boron ester, adjust the pH of the residue to 6-6.5 with sodium hydroxide, and evaporate to dryness under reduced pressure , to obtain 51.22 g of the reduced sulfate product, with a yield of 100%, a fixed nitrogen content of 4.76%, and mp160-163°C.

Embodiment 3

[0026] In the three-necked flask, add 300g (9.36mol) methanol, 50g (0.17mol) D-threo-p-methylsulfonylphenylserine ethyl ester, raise the temperature to 35°C, add 13g (0.24mol) potassium borohydride, and keep warm for 5 hours , and then add 34g (0.301mol) of phosphoric acid to adjust the pH to 1.5-2, keep the temperature at 60-65°C for 3.5-4 hours, evaporate methanol and boron ester, adjust the pH of the residue to 8.5-9.0 with sodium methoxide, and evaporate to dryness under reduced pressure. 50.98 g of the reduced phosphate product was obtained, with a yield of 99.53%, a fixed nitrogen content of 4.74%, and an mp of 155-157°C.

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Abstract

The invention provides a method for preparing a florfenicol intermediate salt, which comprises the following steps of: with D-threo-methylsulfonylphenylserine ethyl in a formula II shown in the specification and potassium borohydride as raw materials and methanol as a solvent, reacting at 35 DEG C for 5 hours; adjusting a pH value to acidity with acid; preserving the temperature for a period of time at heat preservation temperature; distilling; adjusting residues with alkali; and drying to obtain the target compound florfenicol intermediate salt in a formula III shown in the specification. The invention has the advantages that: the process is simple, reaction conditions are mild, is the yield is improved by 2-3 percent higher than that of the relevant document report, the cost is reduced by 1-2 percent lower than that the document report, the used raw materials can not cause environmental pollution, and the like.

Description

technical field [0001] The invention relates to a florfenicol intermediate salt and a boron removal method in the preparation process thereof. Background technique [0002] Florfenicol is a new veterinary-specific chloramphenicol broad-spectrum antibacterial drug successfully developed in the late 1980s. It was first launched in Japan in 1990. It was approved by Norway in 1993 to treat furunculosis in salmon. It was approved in 1995. Approved in France, Great Britain, Austria, Mexico and Spain for the treatment of bovine respiratory bacterial diseases. (I) is a key intermediate for the preparation of Florfenicol. [0003] [0004] (I) [0005] The synthesis of (I) has been reported by patent CN97198768: [0006] [0007] After the reduction reaction, glycerol is used to quench the reduction reaction, and glycerol is used to deboron and serve as a solvent for the next reaction. This process has disadvantages such as difficult recovery of glycerol, high cost, and larg...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/32C07C315/04
Inventor 竺亚庆陈林静李思全童国青郭磊陈小刚
Owner XINCHANG HEBAO BIOTECH
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