Hydroxylamine → HCID 76637602, compound

Participants

Reaction Steps

A solution of benzyl 5-(2-chloroethyl)-3-cyanotetrahydrofuran-3-ylcarbamate (0.86 g, 2.79 mmol) and 50% aq. hydroxylamine (0.853 mL, 13.93 mmol) in THF (25 mL) was stirred at room temperature for 18 h. The mixture was concentrated and the residue was redissolved in EtOH (20 mL) and treated with diethyl acetylenedicarboxylate (0.490 mL, 3.06 mmol) at room temperature. After 24 h, the reaction mixture was concentrated and the resulting pale yellow residue was taken up in Et2O (75 mL), washed with 1% aq. NH4OH (20 mL), water (20 mL) followed by brine (20 mL), then dried (Na2SO4), filtered, concentrated and purified by flash column chromatography on silica gel column using 1:3, 2:3 and 1:1 ethyl acetate/hexane to afford diethyl 2-(amino(3-(benzyloxycarbonylamino)-5-(2-chloroethyl)tetrahydrofuran-3-yl)methyleneaminooxy)but-2-enedioate (1.1707 g, 2.287 mmol, 82% yield) as a pale yellow paste. 1H NMR (500 MHz, CDCl3) δ: 7.30-7.39 (5 H, m), 5.75-5.88 (2 H, m), 5.26-5.62 (2 H, m), 5.05-5.12 (2 H, m), 4.21-4.37 (3 H, m), 4.12-4.20 (3 H, m), 4.02-4.10 (1 H, m), 3.57-3.67 (2 H, m), 2.60-2.85 (1 H, m), 1.87-2.20 (3 H, m), 1.29-1.38 (3 H, m), 1.22-1.28 (3 H, m). LCMS (M+H) calcd for C23H31ClN3O8: 512.18; found: 512.25.

Provenance & Evidence