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.

Structures of benzene and 3-chloronitrobenzene 4

Converting benzene into nitrobenzene 5

Chlorination of an aromatic ring 6

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.

Stereoisomers of thalidomide

Pharmacological activity depends on whether or not a drug can interact with a receptor site in a biological system. 13

Structure of ibuprofen, used in many medicines to relieve pain 14