Triethylamine → HCID 54031289, compound

Participants

Reaction Steps

A solution of 2-(trans-2-carboxycyclopropylthio)-3-phenylquinoline (3.26 g.), diphenylphosphoryl azide (2.21 ml.) and triethylamine (1.43 ml.) in dry toluene (65 ml.) was stirred under argon for 2 hr. at 90°. 2-(Trimethylsilyl)ethanol (1.53 ml.) was added, and the reaction mixture was stirred for a further 16 hr. at 90°. The mixture was cooled to ambient temperature, washed with water (2×20 ml.), dried (Na2SO4), and the toluene removed under reduced pressure. The residual brown oil (5.5 g.) was purified on a basic alumina column (200 gm. Brockmann Grade III) by elution with 20% v/v chloroform in petroleum ether to give 2-{trans-2-[2-(trimethylsilyl)ethoxycarbonylamino]cyclopropylthio}-3-phenylquinoline as a light yellow oil, which was characterised by mass spectrometry, molecular ion equals 436, and by NMR (CDCl3 solution, 90 MHz) multiplet 2.5 δ (2H, cyclopropane methine).

Provenance & Evidence