Protected DO3A Ester One-Step Isolation via Water Dilution
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Solution Overview
Problem
Existing methods for preparing DO3A-tri-tert-butyl ester as a hydrobromide salt are time-consuming and require complex purification processes, making them unsuitable for large-scale industrial production.
Innovation Solution
A one-step process involving the dilution of the crude reaction mixture with water after reacting 1,4,7,10-tetraazacyclododecane with tert-butyl bromoacetate in an organic solvent and the presence of a base, allowing for the direct collection of DO3A-tri-tert-butyl ester as a solid salt.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If traditional multi-step purification procedures are used, then product purity is improved, but manufacturing time and process complexity increase
Solution Approach 1:
The invention extracts and isolates the desired DO3A-tri-tert-butyl ester hydrobromide salt directly from the crude reaction mixture by selective precipitation upon water addition. This single extraction step replaces traditional multi-step purification procedures, achieving high purity (95-99.5%) while dramatically reducing manufacturing time and process complexity.
Solution Approach 2:
The invention changes the solvent parameters by adding water to the organic reaction mixture, which alters the solubility characteristics of the components. This parameter change causes the hydrobromide salt to precipitate selectively in high purity form, eliminating the need for multiple purification steps while maintaining excellent product quality.
2Manufacturing precision
If traditional multi-step purification procedures are used, then product purity is improved, but process complexity increases
Solution Approach 1:
The invention merges the purification function into the work-up step by combining precipitation and isolation into a single operation. The addition of water simultaneously achieves product isolation and purification, eliminating separate purification steps and significantly simplifying the overall manufacturing process while maintaining high product purity.
Solution Approach 2:
The invention extracts the purified product directly during the work-up phase through selective precipitation. This single extraction operation replaces complex multi-step purification sequences, reducing process complexity while achieving the required product purity level of 95-99.5%.
3Quantity of substance
If reaction time is extended, then product yield is improved, but productivity decreases
Solution Approach 1:
The invention changes the work-up parameters by adding water to precipitate the product, which allows for rapid isolation and recovery of high yields (73-83%). This parameter change enables short reaction times to be as effective as longer reactions, thereby maintaining high productivity while achieving excellent yields.
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 significantly reduces reaction and work-up times, achieving high yields (73-83%) and optimal purity (95-99.5%) of DO3A-tri-tert-butyl ester hydrobromide salt, making it suitable for industrial-scale production without the need for additional purification steps.
Implementation Method 1
adding water to the mixture obtained in step 1), to obtain a suspension comprising the DO3A-tri-tert-butyl ester as solid salt
Data Source
AI summary
The invention relates to a process for the one-step preparation and isolation of a protected DO3A such as DO3A-tri-tert-butyl ester as a solid salt.