Supercharge Your Innovation With Domain-Expert AI Agents!

A kind of preparation method of moxifloxacin intermediate compound

A compound and donor technology, applied in the field of preparation of moxifloxacin intermediate compounds, can solve the problems of low product ee value, complex process and high cost, and achieve the effects of simple operation, few steps and low cost

Active Publication Date: 2022-08-02
SHANGHAI PUYI CHEM CO LTD
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] The technical problem to be solved by this invention is to overcome the key chiral intermediate (4aS, 7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine (I) preparation method of moxifloxacin in the prior art The defects of high cost, complex process and low product ee value in the present invention provide a preparation method of moxifloxacin intermediate compound

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of moxifloxacin intermediate compound
  • A kind of preparation method of moxifloxacin intermediate compound
  • A kind of preparation method of moxifloxacin intermediate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] 1. Transamination reaction

[0062]

[0063] 15.0g of 3-(3-bromopropyl)-4-oxopyrrolidine-1-carboxylate ethyl ester (3-1) was added to 400mL of distilled water, 20mL of DMSO was added to help dissolve, and R- 10.0g of methylbenzylamine and hydrochloric acid adjust the pH of the reaction solution to about 8.0, then add 30.0g of ω-transaminase and 0.08g pyridoxal phosphate (PLP), wherein, the amino acid sequence of ω-transaminase is such as SEQ ID NO in the sequence table .1; keep the temperature at 25-30°C, pH around 8.0, and react for 20 hours, the TLC raw materials are basically reacted completely, and the reaction is stopped. The pH of the system was adjusted to 2-3 with concentrated hydrochloric acid, and after stirring, diatomaceous earth was added for suction filtration, the filter cake was rinsed with water, the filtrate was extracted with dichloromethane, and the pH of the aqueous phase was adjusted to above 10 with 30% aqueous sodium hydroxide solution , and ...

Embodiment 2

[0069] 1. Transamination reaction

[0070]

[0071] Add 10.0g of ethyl 3-(3-chloropropyl)-4-oxopyrrolidine-1-carboxylate (3-2) to 300mL of distilled water, add 15mL of DMSO to dissolve, and add 4.0g under stirring Isopropylamine and hydrochloric acid adjust the pH of the reaction solution to about 9.0, then add 20.0g of ω-transaminase and 0.05g pyridoxal phosphate (PLP), wherein, the amino acid sequence of ω-transaminase is as shown in the sequence table SEQID NO.2; The temperature was raised to 45-50° C., and the pH was kept at about 9.0. After the reaction was maintained for 12 hours, the TLC raw materials basically reacted completely, and the reaction was stopped. The pH of the system was adjusted to 2-3 with concentrated hydrochloric acid, and after stirring, diatomaceous earth was added for suction filtration, the filter cake was rinsed with water, the filtrate was extracted with dichloromethane, and the pH of the aqueous phase was adjusted to above 10 with 30% aqueous...

Embodiment 3

[0076] 1. Transamination reaction

[0077]

[0078] 20.0g of 3-(1-benzyl-4-oxypyrrolidin-3-yl)propylmethanesulfonate (1-3) was added to 600mL of distilled water, and 10.0g of D-alanine and ammonia were added under stirring The pH of the reaction solution was adjusted to about 10.0, then 40g of ω-transaminase and 0.10g of pyridoxal phosphate (PLP) were added, wherein, the amino acid sequence of the ω-transaminase was as shown in the sequence table SEQ ID NO.3; be warming up to 45- At 50° C., keeping the pH at about 10.0, after the reaction was incubated for 2 hours, the TLC raw materials basically reacted completely, and the reaction was stopped. The pH of the system was adjusted to 2-3 with concentrated hydrochloric acid, and after stirring, diatomaceous earth was added for suction filtration, the filter cake was rinsed with water, the filtrate was extracted with dichloromethane, and the pH of the aqueous phase was adjusted to above 10 with 30% aqueous sodium hydroxide solu...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of moxifloxacin intermediate compound. The method comprises the following steps: in a solvent, under the action of ω-transaminase and / or its immobilized form and ammonia donor, the compound shown in formula (III) is subjected to the transamination reaction shown below to obtain the The compound shown in formula (II); the amino acid sequence of described ω-transaminase is as shown in sequence table SEQ ID NO.1, SEQ ID NO.2 or SEQ ID NO.3; Wherein, X is chlorine, bromine, iodine , mesylate or p-toluenesulfonate; R is C 1‑4 Alkoxycarbonyl, benzyloxycarbonyl or benzyl. The preparation method of the invention has low cost, few steps, simple operation, and the ee value of the product is as high as 99% or more, and is more suitable for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of moxifloxacin intermediate compound. Background technique [0002] Moxifloxacin (moxifloxacin) is a third-generation quinolone spectrum antibacterial drug, which has been widely used in clinical treatment of respiratory tract infections such as acquired pneumonia, acute exacerbation of chronic bronchitis, and acute bacterial sinusitis since its launch in 1999. [0003] [0004] (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine (I) is a key chiral intermediate of moxifloxacin, and its molecular structure has two skeleton structures of piperidine and pyrrolidine and two Chiral centers, the reported preparation methods are mainly divided into the following categories: [0005] Route 1: Piperidine Route [0006] [0007] The piperidine route has more reports of synthetic methods, and it is also the technique adopted in the current industrial production. These techniques all use 3,4-pyridinedicarbo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/16
CPCC12P17/165
Inventor 杨汉荣谢凌拾陶荣盛李涛王博
Owner SHANGHAI PUYI CHEM CO LTD
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com