Summary
- Profile Type
- Technology offer
- POD Reference
- TOES20250325004
- Term of Validity
- 25 March 2025 - 25 March 2026
- Company's Country
- Spain
- Type of partnership
- Research and development cooperation agreement
- Targeted Countries
- All countries
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General information
- Short Summary
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Researchers from a Spanish university have described a procedure for the synthesis of hydroxyalkylamide derivatives from the corresponding O-aryl N,N-diethylcarbamates and an epoxide, which has allowed them to prepare several series of new chiral compounds with potential applications in the pharmaceutical industry.
The research group seeks research and development cooperation agreement. - Full Description
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Since 1998, research work in this university group is centred on the development of new methodology in Organic Synthesis. The research group has experience in the preparation of functionalized heterocyclic compounds with potential biological activity.
The described procedure allows the synthesis of new compounds derived from (6-hydroxyphenyl)-N,N-diethyl-3-hydroxyalkylamides from O-aryl N,N-diethylcarbamates as starting substrates, being able to present groups of different chemical nature on the aromatic ring, such as halogens, methoxy groups, or unsubstituted. Likewise, the use of sec-butyllithium or lithium diisopropylamide is required, in tetrahydrofuran, at –78 ºC, atmospheric pressure and in an inert nitrogen gas atmosphere, for the ortho-lithiation reaction of the starting carbamates.
The subsequent addition of lithium 2,2,6,6-tetramethylpiperidide and the addition of a terminal epoxide, which can be alkyl or with a functional group, both racemic and enantiomerically pure, gives rise to the homologous regrouping of Snieckus-Fries 1,4 -O → C of the carbamoyl group by the evolution of the reaction at room temperature for 3 hours.
The potential application of the described procedure is the synthesis of chiral aromatic organic compounds that contain alcohol groups in their structure, as well as halogens and other functional groups, for which they are postulated as highly versatile synthetic intermediates with great applicability in the pharmaceutical, agrochemical, industry. chemistry, etc.
The research group is looking for research and development cooperation agreement. - Advantages and Innovations
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Chiral organic compounds with hydroxyl groups are important synthetic precursors of amino acids, alkaloids, carbohydrates, and other chiral compounds with possible biological and / or pharmacological activity. That is why one of the main challenges of current organic chemistry is the search for new efficient and clean synthesis procedures that allow access to chiral compounds.
The novel procedure described by the UBU researchers makes it possible to obtain a new family of derivatives of (6-hydroxyphenyl)-N,N-diethyl-3-hydroxyalkylamides, which are not described in the literature and which are obtained as a single diastereoisomer. The pharmacological relevance of both chiral organic compounds and epoxides is demonstrated by the fact that they are found or precursors of numerous biologically active compounds or natural products.
Main advantages:
• The process that makes it possible to obtain a new family of derivatives of (6-hydroxyphenyl)-N,N-diethyl-3-hydroxyalkylamides is novel.
• The compounds are not described in the literature and are obtained as a single diastereoisomer.
• The process can also be carried out using chiral epoxides, thus making it possible to obtain the final products in an enantiospecific way. - Stage of Development
- Lab tested
- Sustainable Development Goals
- Goal 9: Industry, Innovation and Infrastructure
- IPR status
- IPR granted
Partner Sought
- Expected Role of a Partner
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Research cooperation agreement:
• Type: research organization and industries.
• Role: drug and chemical products development - Type and Size of Partner
- SME <=10
- SME 11-49
- SME 50 - 249
- Big company
- Other
- Type of partnership
- Research and development cooperation agreement
Dissemination
- Technology keywords
- 03004006 - Organic Substances
- 03004007 - Pharmaceutics
- 05001004 - Organic Chemistry
- 03004001 - Agro chemicals
- Market keywords
- 08001022 - Agricultural chemicals
- 08001017 - Industrial chemicals
- 08001023 - Other chemicals and materials (not elsewhere classified)
- Targeted countries
- All countries