HCID 178449822, compound → HCID 178449783, compound

Participants

Reaction Steps

3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-quinolinyl)propyl 2-[(tert-butoxycarbonyl)amino]-3-methylbutanoate from Example No. 146 (0.13 g) is stirred in a mixture of 4 mL trifluoroacetic acid and 7 mL CH2Cl2 at 0° C. for approximately 1.5 h. Once the reaction is complete, the mixture is partitioned between CH2Cl2 and saturated NaHCO3. After the TFA is neutralized, any undissolved material is filtered off. The organic layer is washed once with water. The combined aqueous layers are back-extracted with CH2Cl2 and EtOAc. The organics are combined, dried over Na2SO4, filtered, and concentrated in vacuo to give a white solid. The solid is recrystallized from a minimal amount of EtOH. (0.040 g, 0.082 mmol, 35%).

Provenance & Evidence