L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)- → tert-Butyl (2,6-dioxopiperidin-3-yl)carbamate

Participants

Reaction Steps

A mixture of N-(tert-butoxycarbonyl)-L-glutamine (4.92 g, 20 mmol) and carbonyl diimidazole (3.24 g, 20 mmol) in THF (100 mL) was refluxed for 16 h. Thereafter, solvent was removed and the crude product was recrystallized from hot EtOAc to give compound 203 (2.04 g, 45%) as white crystals: mp 214-215° C.; 1H NMR (DMSO-d6) δ 4.22 (dd, J=6.2 Hz, J=11.0 Hz, 1H), 2.77-2.65 (m, 1H), 2.45 (m, 1H), 1.96-1.87 (m, 2H), 1.40 (s, 9H); MS (CI/CH4) m/z 227 [M−1]+.

Provenance & Evidence