Vitamin D Derivative Synthesis via UV B-Ring Opening
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
The conventional process for producing the vitamin D derivative [(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl]oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide is hindered by the need for a carbon monoxide-inserting reaction and temperature sensitivity, making it impractical for scaling up, and has low yield and numerous steps.
Innovation Solution
The process involves irradiating a compound with UV to open the B-ring of the steroid skeleton and subsequent isomerization to obtain the desired compound, reducing the number of steps and improving efficiency.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If the conventional process is used to produce the vitamin D derivative, then the compound can be synthesized, but the process requires a carbon monoxide-inserting reaction and temperature control at -15°C or lower, making it difficult to scale up
Solution Approach 1:
The invention changes the reaction parameters by using UV irradiation instead of carbon monoxide insertion, and by conducting the reaction at ambient temperature rather than -15°C or lower. This transforms the process into a scalable manufacturing method while maintaining the desired compound structure.
Solution Approach 2:
The invention replaces the mechanical/chemical system of carbon monoxide insertion with a photchemical system using UV irradiation. This substitution eliminates the need for specialized temperature control equipment and complex reaction monitoring, enabling easier scaling.
2Productivity
If the conventional process is used, then the vitamin D derivative can be produced, but the yield is low and the number of steps is excessive
Solution Approach 1:
The invention extracts and eliminates unnecessary intermediate steps from the conventional synthesis pathway. By using UV irradiation to directly form the target compound structure, the process removes multiple purification and transformation steps, thereby improving yield and reducing production time.
Solution Approach 2:
The invention performs preliminary structural arrangement through UV irradiation that pre-forms the core structure of the vitamin D derivative, eliminating the need for subsequent complex transformation steps and improving overall efficiency.
3Manufacturing precision
If the conventional process is used, then the compound can be synthesized, but the stereoselectivity is sensitive to temperature, requiring strict temperature control
Solution Approach 1:
The invention changes the temperature parameter from strict control at -15°C or lower to ambient temperature operation. This parameter change maintains stereoselectivity while dramatically simplifying temperature control requirements, making the process suitable for industrial scaling.
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 approach results in a more practical and efficient production process with higher yield, overcoming the limitations of the conventional method by simplifying the synthesis and increasing scalability.
Implementation Method 1
irradiating a compound represented by Formula (2) with UV to open the B-ring of the steroid skeleton
Implementation Method 2
isomerizing the resulting compound to obtain the compound of Formula (1)
Data Source
AI summary
There are provided a novel process for producing [{(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is characterized by irradiating a compound represented by the formula:with UV to ring-open the compound, and then isomerizing the resulting compound; an intermediate useful for carrying out the process; and a process for producing the intermediate.