L-2-Amino-4-Halobutyric Acid Derivative Tartrate Resolution
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Solution Overview
Problem
Current methods for synthesizing L-glufosinate are inefficient, costly, and difficult to industrialize due to the lack of a simple and cost-effective process for producing chiral aminobutyric acid blocks, particularly through the resolution of racemic aminobutyric acid derivatives.
Innovation Solution
A method involving the preparation of L-2-amino-4-halobutyric acid derivative-L-tartrate through resolution reactions using L-tartaric acid or a combination of L-tartaric acid, aromatic aldehydes, and organic acids, allowing for the production of stable chiral intermediates via dynamic or static resolution processes.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If chemical resolution methods using quinine or ephedrine analogues are used to prepare L-glufosinate, then L-glufosinate can be obtained, but the process becomes expensive and difficult to industrialize due to low yield and high cost of resolving agents
Solution Approach 1:
The patent replaces expensive, controlled substances (ephedrine analogues) and costly natural products (quinine) with inexpensive, readily available L-tartaric acid as the resolving agent. L-tartaric acid is a common food additive that can be used in large quantities without special handling requirements, making the process economically viable for industrial-scale production while maintaining high optical purity of the L-glufosinate product
Solution Approach 2:
The patent optimizes reaction parameters including the molar ratio of L-tartaric acid to racemic aminobutyric acid derivative (1:1 to 2:1), reaction temperature (0°C to room temperature), and solvent selection (water, ethanol, or their mixtures) to maximize the yield and optical purity of L-glufosinate while keeping the process simple and industrially feasible
2Manufacturing precision
If complex resolution processes with multiple steps are used, then L-glufosinate can be produced with high optical purity, but the process complexity increases and production efficiency decreases
Solution Approach 1:
The patent combines the resolution step with the existing synthesis pathway by directly adding L-tartaric acid to the racemic aminobutyric acid derivative intermediate. This integrated approach eliminates the need for separate resolution, purification, and recrystallization steps required by traditional methods, reducing process complexity while maintaining high optical purity and improving production efficiency
Solution Approach 2:
The patent selectively extracts the L-enantiomer from the racemic mixture through direct salt formation with L-tartaric acid. The L-tartaric acid forms a soluble salt with the L-aminobutyric acid derivative that can be easily separated from the D-enantiomer through filtration and crystallization, achieving high optical purity in a single efficient step
3Manufacturing precision
If traditional resolution agents like quinine are used, then L-glufosinate can be obtained, but the cost increases significantly and the process becomes unsuitable for large-scale production
Solution Approach 1:
The patent replaces expensive, controlled substances (ephedrine analogues) and costly natural products (quinine) with inexpensive, readily available L-tartaric acid as the resolving agent. L-tartaric acid is a common food additive that can be used in large quantities without special handling requirements, making the process economically viable for industrial-scale production while maintaining high optical purity of the L-glufosinate product
Solution Approach 2:
The patent enables easy recovery and recycling of L-tartaric acid from the reaction mixture and mother liquors through crystallization and filtration. The resolved D-enantiomer can also be racemized and reused, minimizing waste and further reducing production costs compared to methods using expensive, non-recyclable resolving agents
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
Provides a cost-effective and industrially feasible process for producing chiral aminobutyric acid blocks, which are stable and can be easily converted into L-glufosinate, reducing production costs and environmental impact.
Implementation Method 1
mixing a D, L-2-amino-4-halobutyric acid derivative enantiomeric mixture, L-tartaric acid, and a solvent to facilitate a resolution reaction and produce a resolution reaction mixture comprising L-2-amino-4-halobutyric acid derivative-L-tartrate
Implementation Method 2
precipitating the L-2-amino-4-halobutyric acid derivative-L-tartrate
Data Source
AI summary
The present disclosure describes an L-S2-amino-4-halobutyric acid derivative-L-tartrate salt. The present disclosure also describes a method of preparing L-S-amino-4-halobutyric acid derivative-L-tartrate salt, comprising the following steps: using D, L-S2-amino-4-halobutyric acid derivative enantiomeric mixture as the raw material, using L-tartrate as the resolution agent, and obtaining L-S2-Amino-4-halobutyric acid derivative-L-tartrate by resolution reaction, crystallization and filtration in the same resolution agent system; or the enantiomeric mixture of D, L-S2-amino-4-halobutyric acid derivatives is used as raw material, L-tartrate is used as resolution agent under aromatic aldehyde catalysis or aromatic aldehyde and organic acid co-catalysis, and dynamic resolution reaction is carried out in the same resolution agent system, further comprising crystallization and filtration to obtain L-S2-amino-4-halobutyric acid derivative-L-tartrate.