Sodium Azide → (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyltetrazolo[1,5-a]quinolin-7-yl)ethyl pivalate

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The mixture of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26)(30 mg) and sodium azide (32 mg) in DMF (1 mL) was heated at 90° C. for 4 hours. The mixture was diluted with ethyl acetate, and washed with water and brine, and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexanes/EtOAc) gave (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyltetrazolo[1,5-a]quinolin-7-yl)ethyl pivalate (5.9 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C27H32ClN4O3: 495.2. Found: 495.2.

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