Coupling of 1,3-dimethylindole-2-carboxylic acid (II) with 5-fluoro-4-hydroxy-3-(valinylamino)pentanoic acid tert-butyl ester (I) using EDC in the presence of DMAP furnished amide (III). Subsequent Swern oxidation of the hydroxyl group of (III) gave ketone (IV). The tert-butyl ester of (IV) was finally cleaved by treatment with trifluoroacetic acid.