In a related procedure, the title hydroxy ketone was obtained from hydroxy acid (III) and trifluoroacetic anhydride.
The title compound was obtained by several synthetic procedures. The Dakin-West reaction of N-benzoyl-N-methylphenylalanine (I) with trifluoroacetic anhydride and pyridine produced the intermediate alpha-amino ketone (II), which underwent easy hydrolysis to the required hydroxy ketone via the enolic form of amino ketone (II).
Alternatively, acylation of tert-butyl methyl hydrazone (IV) with trifluoroacetic anhydride in pyridine produced the diaza alkadiene (V). Subsequent acid hydrolysis of (V) gave rise to the desired alpha-hydroxy ketone.