Ammonia → HCID 54202893, compound

Participants

Reaction Steps

(+)-2-(3-(2-(7-Chloroquinolin-2-yl)ethenyl)phenoxy)propanoic acid from Example 72 (2.372 g, 6.71 mmol) was dissolved in methylene chloride (40 mL) containing triethylamine (1.87 mL, 12.5 mmol), and ethyl chloroformate (710 μL, 7.38 mmol) in methylene chloride (20 mL) was added dropwise at -15° C. with stirring. The mixture was stirred for a further 20 minutes at -15° C., and then it was poured into methylene chloride (125 mL) that had been saturated with ammonia at 0° C. The reaction mixture was stirred for a few minutes, and then poured into ice-water The mixture was filtered, and the filtrate was separated. Evaporation of the methylene chloride layer gave more solid, and the two fractions were combined and recrystallized from acetonitrile to give the title product, mp 195°-197° C., [α]D -9.8° (c 0.515 in dimethylformamide).

Provenance & Evidence