Diethyl acetylenedicarboxylate → HCID 86634931, compound

Participants

Reaction Conditions

Reaction Steps

To benzyl 2-amino-2-(hydroxyimino)-1-(3-(hydroxymethyl)cyclopentyl)ethyl(methyl)carbamate (0.800 g, 1.78 mmol) in EtOH (40 mL) was added diethylacetylenedicarboxylate (0.428 ml, 2.67 mmol). The reaction mixture was stirred at 23° C. for 2 days. The solvent was removed in vacuo and the crude material purified on a Silica gel column (Biotage flash chromatography system), eluted with a gradient of ethyl acetate:hexane (1:5) to (1:1) to afford 0.570 g (52% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.33-7.42 (5 H, m), 5.17-5.25 (3 H, m), 4.12-4.40 (4 H, m), 3.55 (2 H, m), 2.83-2.94 (4 H, m), 2.70-2.75 (1 H, m), 2.17-2.09 (2 H, m), 1.82-2.00 (3 H, m), 1.21-1.342 (7 H, m). LCMS (+ESI, M+H+) m/z 506.

Provenance & Evidence