2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → Ethyl (N-{2-[(tert-butoxy)carbonylamino]acetylamino}carbamoyl)formate

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Reaction Steps

To a solution of ethyl 2-hydrazinyl-2-oxoacetate (9-2) (0.516 g, 3.91 mmol) in dichloromethane (14 mL) was added EEDQ (0.78 g, 3.175 mmol) at room temperature and it was stirred for 15 min. Then 2-(tert-butoxycarbonylamino)acetic acid (9-3) (0.55 g, 3.175 mmol) was added. The mixture was stirred at room temperature for overnight. Solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel with gradient eluant (PE/EA=3/1 to 1/1). The product was obtained as a white solid (0.787 g, 85%). 1H NMR (400 MHz, CDCl3) δ 9.35 (s, 1H), 8.99 (s, 1H), 5.19 (s, 1H), 4.40 (dd, J=21.7, 7.2 Hz, 2H), 3.93 (d, J=6.1 Hz, 2H), 1.57-1.32 (m, 12H); LRMS (ESI) calculated M+Na for C11H19N3NaO6: 312.2. Found: 312.1.

Provenance & Evidence