Chem 634 Advanced Organic Chemistry Synthesis and Reactivity Prof Joseph Fox Chemical Database Searching Handout 6 Handout 6 Functional Group mapping using Beilstein In this tutorial we will demonstate how to use Beilstein to search with reaction mapping For this specific search we will search for reactions of the type below to find if derivatives of amino acids can be prepared by oxidation of a phenyl group We will proceed by telling the database that we want the quaternary carbon of the phenyl group to end up as the carbonyl carbon of the acid OH NR2 R R NR2 O R R NOTE searches of this type while useful are far from perfect Remember this database is only as good as the person entering the information These searches can also tend to be time consuming Thus for reaction mapping it is often more useful to conduct searches as demonstrated in Scheme 5 where we exercise a little patience in skimming through the hits 1 Begin by drawing the picture shown below as we have done before 2 In reaction editor mode select the pencil 3 Draw a line that connects the quaternary phenyl carbon with the carbonyl carbon of the product 4 You should see a dashed line connecting these atoms This tells the database that this carbon of the reactant is that same carbon atom in the product 5 Begin the search 6 This search produces 40 hits Try selecting hit 14 7 Here we see an example of using RuCl3 NaIO4 to oxidize a phenyl to a carboxylic acid to produce a protected amino acid derivative
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