Aminoisobutyric acid → HCID 53491902, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-bromo-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (1.2 g, 2.94 mmol), 2-aminoisobutyric acid (1.20 g, 12 mmol), copper (I) iodide (0.34 g, 1.76 mmol), N,N-dimethylglycine hydrochloride (0.33 g, 2.35 mmol) and potassium carbonate (1.22, 8.82 mmol) in DMSO (10 mL) was heated for 4 hours at 120° C. After cooling to room temperature, the mixture was treated with ethyl acetate (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded 2-[3-(1-carboxy-1-methyl-ethylamino)-phenyl]-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (300 mg, 24%) as a white solid: LC/MS m/e calcd for C23H27ClN2O4 (M+H)+: 431.9, observed: 431.1.

Provenance & Evidence