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A kind of preparation method of Florfenicol intermediate

A florfenicol and intermediate technology, which is applied in the field of chemical synthesis, can solve the problems of long synthesis steps, low overall yield, complicated operation and the like of florfenicol intermediate B, and achieves high atom utilization rate and short process route. , the effect of simple reaction operation

Active Publication Date: 2021-02-09
京山瑞生制药有限公司
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Problems solved by technology

[0008] Using the above route to prepare Florfenicol intermediate B, there is a large amount of waste water produced by copper salts in production, and because compound 4 is obtained by splitting, the utilization rate of atoms is only half, and the overall yield is low. The whole Florfenicol The synthetic steps of test intermediate B are longer and the operation is more complicated

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  • A kind of preparation method of Florfenicol intermediate
  • A kind of preparation method of Florfenicol intermediate
  • A kind of preparation method of Florfenicol intermediate

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Embodiment Construction

[0028] The invention discloses a preparation method of Florfenicol intermediate (1R, 2R)-2-amino-1-(4-methylsulfonyl)phenyl)propane-1,3-diol, which uses p-methylsulfone Phenylbenzaldehyde is used as a starting material, and it is prepared through asymmetric addition reaction and hydrogenation reaction. The preparation route is as follows:

[0029]

[0030] The present invention adopts p-thiamphenicyl benzaldehyde and nitroethanol in Cu(OTf) 2 Synthesis of (1R, 2R)-1-(4-(methylsulfonyl)phenyl)-2-nitropropane-1,3-diol (compound A) under the catalysis of / L complex, and then add Reaction after hydrogen affords Florfenicol intermediate (1R, 2R)-2-amino-1-(4-methylsulfonyl)phenyl)propane-1,3-diol (compound B), the Cu( OTf) 2 / L catalyst is copper salt complex, copper salt complex Cu(OTf) 2 / L by Cu(OTf) 2 Prepared by refluxing the toluene solution and ligand L in alcohol, Cu(OTf) 2 The molar ratio with ligand L is 2:1, and the structure of ligand L is as follows:

[0031] ...

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Abstract

The invention discloses a preparation method of a florfenicol intermediate. The preparation method comprises the following steps: methylsulfonyl benzaldehyde and nitroethanol undergo an asymmetric addition reaction under the catalysis of a copper salt complex formed by Cu(OTf)2 and a chiral ligand L, and palladium-carbon catalyzed hydrogenation is carried out to obtain the above compound. The preparation method adopting the above route has the advantages of simplicity in operation, environmental friendliness, and broad application prospect.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of Florfenicol intermediate (1R, 2R)-2-amino-1-(4-methylsulfonyl)phenyl)propane-1,3-diol . Background technique [0002] Florfenicol, whose English name is Florfeniol, is a kind of veterinary-specific broad-spectrum antibacterial drug of chloramphenicol developed by Schering-Plough Company of the United States. At present, it is widely used in aquaculture and animal husbandry industries, and is used to treat bacterial diseases such as fish, pigs, and cattle. Its structural formula is as follows: [0003] [0004] At present, the reported synthesis methods mainly include the following two methods: (1) prepare the florfenicol intermediate (B) through ester reduction of D-thymphenyl phenylserine ethyl ester, and then react with benzyl cyanide to close the ring , hydroxyl fluorination reaction, hydrolysis reaction, dichloroacetylation reaction, etc. to prep...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/04C07C317/32C07C317/22
CPCC07B2200/07C07C315/04C07C317/32C07C317/22
Inventor 周国朝钟旭辉张治国徐相雨
Owner 京山瑞生制药有限公司
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