Sulphonylacetic Acid Ester Acyl Donor for Enzymatic Amine Resolution
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Existing methods for the enzymatic resolution of amines using esters as acyl donors suffer from variable selectivities, long reaction times, and high enzyme requirements, making them unsuitable for industrial applications.
Innovation Solution
A process involving the reaction of a chiral amine with a sulphonylacetic acid ester in the presence of a hydrolase, followed by separation of the enantiomerically enriched amide, using a sulphonylacetic acid ester as the acyl donor, which allows for high enantioselectivity and reactivity, and is suitable for various substrates at high concentrations.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional esters (ethyl acetate, ethyl decanoate) are used as acyl donors, then the reaction can proceed with available substrates, but the reaction times are excessively long (5-60 hours or even 5-21 days) and conversions are low (20-44%)
Solution Approach 1:
The patent changes the chemical structure parameters of the acyl donor from conventional esters to sulphonylacetic acid esters. This structural modification fundamentally alters the reactivity parameters, enabling high conversions (90-99%) within 2-18 hours, thus resolving the contradiction between productivity and time loss.
2Productivity
If high enzyme amounts are used to achieve acceptable conversions, then the reaction can proceed, but the process becomes economically unviable with enzyme requirements exceeding 10 000 000 units per mole of substrate
Solution Approach 1:
The patent changes the chemical parameters of the acyl donor to sulphonylacetic acid esters, which inherently possess higher reactivity. This allows the reaction to achieve high conversions with minimal enzyme catalyst, making the process economically viable without requiring excessive enzyme amounts.
3Manufacturing precision
If conventional acyl donors are used, then the process can be simple, but the enantioselectivity varies widely and is often insufficient for industrial applications
Solution Approach 1:
The patent changes the chemical parameters of the acyl donor to sulphonylacetic acid esters, which provide consistent and high enantioselectivity (90-99% ee) across different substrates. This resolves the contradiction by achieving high manufacturing precision without significantly increasing process complexity.
4Productivity
If substrates are used at high concentrations for industrial efficiency, then productivity improves, but many conventional enzymatic reactions require dilute conditions
Solution Approach 1:
The patent changes the chemical parameters of the acyl donor to sulphonylacetic acid esters, which maintain high reactivity and enzyme compatibility even at elevated substrate concentrations. This enables industrial-scale productivity while using practical substrate concentrations.
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
This process achieves high enantiomeric excesses and space/time yields, reducing enzyme and solvent costs, and enabling efficient separation of enantiomers, making it more economical and ecologically friendly.
Implementation Method 1
reaction of a chiral amine with an ester in the presence of a hydrolase
Implementation Method 2
hydrolase and subsequent separation
Data Source
AI summary
The present invention relates to a process for the preparation of enantiomerically enriched amines by cleavage of a racemic mixture of a reaction product of a chiral amine and an acyl donor or reaction of an amine with an acyl donor in the presence of a hydrolase and subsequent separation of the enantiomerically enriched amide from the enantiomerically enriched amine.