HCID 11394853, compound → HCID 86601464, compound

Participants

Reaction Steps

tert-butyl 3-acetoxy-2-(acetoxymethyl)-1-oxo-1-phenylpropan-2-ylcarbamate (2) (420 mg, 1.1 mmol, 1.0 equiv.) was added to a 100 mL RBF and a 4.0 N HCl-Dioxane solution (8.3 mL, 33.0 mmol, 30.0 equiv) was added. The solution was stirred for 25 min and the solvent was evaporated with a steady stream of N2 (g). The resulting residue was taken up in Et2O (40 mL) giving a sticky solid. The mixture was cooled by partial evaporation and the solid was triturated and stirred for 10 min. The precipitate was filtered, washed with Et2O (2×50 mL), and dried under vacuum to give 180 mg (53%) of 4 as a white solid. mp=122-123° C.; 1H NMR (500 MHz, DMSO) δ 9.01 (br s, 3H, C—NH3), 7.97 (d, J=7.0 Hz, 2H, Ph-H), 7.72 (t, J=7.5 Hz, 1H, Ph-H), 7.58 (t, J=7.5 Hz, 2H, Ph-H), 4.78 (AB, J=12.5 Hz, 2H, CCH2), 4.66 (AB, J=12.5 Hz, 2H, C—CH2), 1.97 (s, 6H, (O═C—CH3)2); 13C NMR (125 MHz, DMSO) δ 193.8, 169.4, 133.7, 133.6, 129.0, 128.2, 67.2, 62.8, 20.4; LRMS (ESI-MS m/z): Mass calcd for C14H18NO5 [M]+, 280.30. Found 280.

Provenance & Evidence