Hydrochloric Acid → 2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide

Beteiligte Stoffe

Reaktionsschritte

0.86 ml of Triethylamine, 0.672 g of 1-hydroxy-7-azabenzotriazole and 0.946 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide.HCl were added at R.T. to a suspension of 1.35 g of (3-bromo-quinolin-6-yloxy)-methylsulfanyl-acetic acid in 11 ml of dry DMF. To this suspension, 0.494 g of 2-amino-3-hydroxy-2-methyl-propionitrile dissolved in 2 ml of dry DMF were added dropwise. The reaction mixture was stirred 16 hrs at R.T and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure 1.886 g of a crude mixture were isolated as a dark orange oil. The crude mixture was purified by flash chromatography on silica gel (hexane/ethyl acetate) to give 1.103 g of 2-(3-bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide in mixture with 3-(3-bromo-quinolin-6-yl)-2-methylsulfanyl-propionic acid 2-[2-(3-bromo-quinolin-6-yloxy)-2-methylsulfanyl-acetylamino]-2-cyano-2-methyl-ethyl ester resulting from the homo coupling process.

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