5. Naproxen is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation of various kinds,...
5. Naproxen is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation of various kinds, and is the active ingredient in the over-the-counter drug called Aleve. It operates by inhibiting the enzyme cyclooxygenase (COX) similarly to the more common ibuprofen, but does so with a stronger binding affinity The following pathway shows one example of a multistep synthesis that has been used to access naproxen. a Provide the missing intermediates, reagents, or major organic product in each box provided. You do not need to show any curved-arrow mechanisms Note: We have not learned some of the reactions that were involved in this synthesis. You are not responsible for knowing these reactions, and you do not need to look anything up outside of what we have covered in class to correctly answer this question two steps) (various steps) 2. H* workup naproxen b. Although shown in the synthetic pathway on the previous page, formaldehyde (CH20) is actually troublesome to use as a reagent in synthesis because it is a volatile, toxic gas. More often, chemists will employ the compound trioxane, which in addition to being a more conveniently handled solid, forms three equivalents of formaldehyde in the presence of catalytic acid. This chemical transformation is shown below, provide a complete curved arrow mechanism H cat 0. 0 trioxane formaldehyde