Quinaldic Acid → Quinoline-2-carbonyl-(L)-asparagine tert-butyl Ester

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Reaction Steps

Analogously to Example 100, 5.45 g (31.4 mmol) of quinaldic acid in 161 ml of THF are reacted with 7.08 g (34.3 mmol) of DCC, 4.63 g (34.3 mmol) of HOBT and 5.38 g (28.6 mmol) of (L)-asparagine tert-butyl ester (Bachem, Bubendorf/Switzerland). Filtration, extraction and column chromatography (SiO2, ethyl acetate/hexane 3:1) yields the pure title compound: TLC Rf (C')=0.15; tRet (V)=12.2 min; FAB-MS (M+H)+ =344.

Provenance & Evidence