Di-tert-butyl dicarbonate → HCID 86626940, compound

Participants

Reaction Steps

N,N-di[2-(4-methoxycarbonyl-2-methoxy-5-nitrophenyl-oxy)ethyl]amine, compound 9, (crude, 4.16 mmol) and NaHCO3 (210 mg, 2.50 mmol) was suspended in THF, and treated with (BOC)2O (999 mg, 4.58 mmol) at 0° C. and stirring was continued at rt for 3 h. After removal of THF, the residue was partitioned between H2O and EtOAc (100/100 mL). Aqueous layer was further extracted with EtOAc (2×50 mL). The combined EtOAc layers were washed with brine (80 mL), dried (MgSO4), and concentrated. Purification of the residue by flash chromatography (silica gel, 6:4 hexanes/EtOAc) yielded N-tert-butoxycarbonyl-N,N-d i[2-(4-methoxycarbonyl-2-methoxy-5-nitro-phenyloxy)ethyl]amine, compound 10, as light yellow solid: 1HNMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 3.77 (m, 4H), 3.83, 3.86 and 3.87 (3×s, 12H), 4.20 and 4.26 (2×t, J=3.9 Hz, 4H), 6.97 and 6.99 (2×s, 2H), 7.36 and 7.40 (2×s, 2H); EIMS m/z 646 ([M]++Na).

Provenance & Evidence