Hydroxylamine → tert-butyl (2R)-2-[[2-[tert-butyl(dimethyl)silyl]oxy-1-[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]ethyl]amino]propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl N-[2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-cyanophenyl)ethyl]-D-alaninate (2 g, 0.0049 mol) in Ethanol (40 ml) was added 50% aqueous Hydroxylamine (1.63 ml, 0.0247 mol) at RT. The reaction mixture was heated at 70° C. for 6 h, cooled to RT and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, brine, dried over Na2SO4 and evaporated to afford (2 g, 90%) of the title compound as brown oil. 1H NMR: (DMSO-d6, 400 MHz) δ 9.57 (s, 1H), 7.61-7.59 (d, J=8.3 Hz, 2H), 7.30-7.28 (d, J=8.3 Hz, 2H), 5.76-5.74 (d, J=5.00 Hz, 2H), 4.77-4.74 (m, 1H), 3.21-3.19 (m, 1H), 2.69-2.59 (m, 1H), 1.95-1.72 (m, 1H), 1.39 (s, 9H), 1.10-1.06 (m, 3H), 0.86-0.82 (m, 9H), 0.03 (s, 3H), −0.12 (s, 3H). LC/MS (Method A): 438.3 (M+H)+. HPLC (Method A) Rt 3.82 min. (Purity: 71.1%).

Provenance & Evidence