A process is provided for preparing a dipeptidyl peptidase IV inhibitor of
the structure 1
wherein 2
is treated with TFAA in isopropyl acetate to protect the tertiary hydroxyl
group as a trifluoroacetate group to form 4 3
(which is a novel intermediate)
which is converted to acid chloride compound 5 4
(which is a novel compound)
using Vilsmeier reagent or other chloro reagent and coupled with compound
6 in a heterogeneous mixture of ethyl acetate and aqueous bicarbonate to
give compound 7 5
The N,O-bis(trifluoroacetyl) groups of compound 7 are deprotected to give
free base compound 10.