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PHAY0006 Chemical Synthesis workshop (2).pdf
- 1. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Chemical Synthesis Workshop Stephen Hilton s.hilton@ucl.ac.uk
- 2. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Forward Synthesis R OH Halide Formation - Alcohol to Halide Br R HBr R Br Alcohol Formation - Halide to Alcohol OH R NaOH Note the type of halide is important as elimination will occur in the case of secondary or tertiary halides R Br Primary Amine Formation - Halide to Amine NH2 R NH3 R Br Secondary/ Tertiary Amine Formation - Halide to secondary or tertiary Amine N R N H R 2 2 R 1 1 R 2 2 R 1 1 Remember reaving group
- 3. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Forward Synthesis NH2 R N H R Secondary Amine formation - primary to secondary R 1 1 X R 1 1 X = I, Cl, Br N H R N R Tertiary Amine formation - secondary to tertiary R 1 1 X R 1 1 X = I, Cl, Br R 3 3 R 3 3 NH2 R N H R Amine to amide - primary or secondary react in the same way R 1 1 X R 1 1 X = Cl, Br O O NH2 R N H R S Amine to sulfonamide - primary or secondary amines react in the same way X = Cl, Br O O R 2 2 O S O X R 2 2
- 4. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Forward Synthesis
- 5. steps for chemical synthesis ① know functional groups ① keep it simple ③ Do not rush ④ Do ¥0 thing yii.io don't know ⑤ recognise the nucleophile and electrophile
- 6. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Forward Synthesis
- 7. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Outline a one-step retrosynthesis of the following compounds using a disconnection approach Retrosynthesis / " .
- 8. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Outline a one-step retrosynthesis of the following compound using a disconnection approach Retrosynthesis Outline a two-step retrosynthesis of the following compound using a disconnection approach OH = 0 ] equivalence
- 9. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Retrosynthesis – 2-step disconnection
- 10. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Retrosynthesis Exam question I
- 11. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Retrosynthesis of Chloroquine
- 12. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Fexofenadine analogue retrosynthesis N OH O O CH3 OH O HO
- 13. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Retrosynthesis Assuming the yield from each step is 70% - calculate the overall yield starting from the aldehyde
- 14. UCL SCHOOL OF PHARMACY BRUNSWICK SQUARE Retrosynthesis If company A wanted to make 100 analogues of the final molecule by changing the aromatic ring shown in red, would you suggest changing the synthetic route? If yes, how would you change it?