Boc-L-Valine → HCID 178449822, compound

Participants

Reaction Steps

N-Boc-valine (0.13 g) is added to a solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-quinolinecarboxamide from example 110 (0.15 g), EDC hydrochloride (0.11 g), and DMAP (0.016 g) in 4 mL pyridine. The reaction is stirred at room temperature overnight. The solvent is removed in vacuo and the residue partitioned between CH2Cl2 and H2O. The organic layer is washed once with water, and once with brine. The organic layer is then dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow liquid. The residue is adsorbed onto silica and purified by chromatography on a Biotage Flash 40S column (eluent 1% MeOH:CH2Cl2 (1 L) followed by 2% MeOH:CH2Cl2 (2 L)). The product is obtained as a white solid which is further purified by recrystallization with CH2Cl2 /hexanes (0.17 g, 74%).

Provenance & Evidence