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Starter. Suggest a two-step synthesis for 3-aminopropanoic acid from 3-bromopropanol. Suggest a two step synthesis for butanol acid from ethyl butanoate. Organic Synthesis of aromatic compounds. L.O.: Devise multi-stage synthetic routes for preparing aromatic organic compounds.
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Starter • Suggest a two-step synthesis for 3-aminopropanoic acid from 3-bromopropanol. • Suggest a two step synthesis for butanol acid from ethyl butanoate.
Organic Synthesis of aromatic compounds L.O.: Devise multi-stage synthetic routes for preparing aromatic organic compounds.
Task: Propose a retro-synthesis of paracetamol
Chirality in pharmaceutical synthesis • Explain that the synthesis of pharmaceuticals often requires the production of a single optical isomer. • Explain that synthetic molecules often contain a mixture of optical isomers, whereas natural molecules often have only one optical isomer. • Explain that the synthesis of a pharmaceutical that is a single optical isomer increases costs, reduces side effects and improves pharmacological activity. • Describe strategies for the synthesis of a pharmaceutical with a single optical isomer.
Very potent M3 antagonist. Clinical candidate for COPD Task: • Dr Bravo synthesised the above compound as a mixture of enantiomers. In pairs discuss the disadvantages of using the mixture of enantiomers as a clinical candidate for COPD. • In pairs discuss possible solutions to overcome the problems aforementioned.
Disadvantages: • One of the enantiomers may have a harmful effect • Larger dose needed. 2) • Purifying the mixture using chiral HPLC • Synthesise a single chiral isomer
Modern chiral synthesis How to prepare a single chiral isomer: • Using enzymes. • Chiral pool synthesis (starting from chiral molecules) • Use transition element complexes.
Pharmacological activity depends on whether or not a drug can interact with a receptor site in a biological system.
Structure of ibuprofen, used in many medicines to relieve pain