Salcaprozic Acid Synthesis via Active-Ester Amide Formation
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Solution Overview
Problem
Existing processes for manufacturing 8-[(2-hydroxybenzoyl)amino]octanoic acid are not economically efficient, safe, and not well-suited for large-scale production, lacking sustainability and generating hazardous waste.
Innovation Solution
A chemical process involving the reaction of 8-amino caprylic acid or its derivatives with salicylic acid derivatives under mild conditions using readily available starting materials and safe solvents, followed by precipitation and isolation, suitable for both batch and continuous production.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional methods for producing 8-[(2-hydroxybenzoyl)amino]octanoic acid are used, then production can proceed with existing processes, but the processes are not economically efficient, generate hazardous waste, and are not well-suited for large-scale production
Solution Approach 1:
The patent changes the chemical reaction parameters by using a two-step process: first forming an active ester intermediate with N-hydroxysuccinimide and a coupling agent (EDC or DCC), then reacting with the amine. This parameter change in the reaction mechanism eliminates hazardous waste while maintaining economic efficiency and scalability for large-scale production of 8-[(2-hydroxybenzoyl)amino]octanoic acid
Solution Approach 2:
The patent introduces an active ester intermediate (N-hydroxysuccinimide ester) as a mediator in the synthesis process. This intermediate allows the reaction to proceed through a safer, more controlled pathway that avoids hazardous waste generation while being economically efficient and suitable for large-scale manufacturing
2Reliability
If existing synthesis processes are used, then production can continue with current methods, but they lack sustainability and environmental friendliness
Solution Approach 1:
The patent converts the potentially harmful direct coupling reaction into a beneficial two-step process using active ester intermediates. This approach transforms a hazardous reaction into a sustainable, environmentally friendly process that maintains high reliability for producing 8-[(2-hydroxybenzoyl)amino]octanoic acid without generating hazardous waste
3Productivity
If conventional amide formation methods are used, then the reaction can proceed directly, but the process is not cost-efficient and not suitable for production scale
Solution Approach 1:
The patent segments the amide formation reaction into two distinct steps: (1) formation of the active ester intermediate with N-hydroxysuccinimide, and (2) reaction of the intermediate with the amine. This segmentation improves both productivity and cost efficiency by allowing each step to be optimized independently and facilitating scalable production of 8-[(2-hydroxybenzoyl)amino]octanoic acid
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
The process is environmentally friendly, cost-effective, and suitable for large-scale production, reducing hazardous waste generation and improving the efficiency of 8-[(2-hydroxybenzoyl)amino]octanoic acid production.
Implementation Method 1
a method for producing 8-[(2-hydroxybenzoyl)amino]octanoic acid or a derivative thereof comprising the step of reacting 8-amino caprylic acid or a derivative thereof with a salicylic acid derivative
Data Source
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AI summary
The present invention relates to a chemical process for the synthesis of the compound 8-[(2-hydroxybenzoyl)amino]octanoic acid or a derivative thereof useful in the process of making sodium 8-[(2-hydroxybenzoyl)amino]octanoate (SNAC), a delivery agent used in solid pharmaceutical compositions. The invention provides an efficient synthesis using less hazardous chemicals and/or a reproducible process that is easier to handle on production scale.