Hydrochloric Acid → HCID 59066423, compound

Participants

Reaction Steps

HCl gas was bubbled into a solution of N-{2-[(4S)-2-oxo4-benzyl(1,3-oxazolidin-3-yl)]-2-oxoethyl}(tert-butoxy)-N-methylcarboxamide (7.2 g, 21 mmol) in Et2O (150 mL) over 30 min. The resulting white slurry was stirred for 2 h, allowed to warm to room temperature, and stirred for 2 h. A solution of HCl (1M in Et2O, 20 mL, 20 mmol, 3.6 equiv) was added and the reaction mixture was stirred overnight, then treated with TFA (10 mL), and stirred for 2 h. HCl gas was again bubbled into the mixture over 15 min, and the reaction was stirred for 3 h. The resulting mixture was concentrated under reduced pressure and the residue was triturated (100 mL of 50% EtOAc/hexanes). The resulting precipitate was filtered and washed with hexanes to give (4S)-3-[2-(methylamino)acetyl]-4-benzyl-1,3-oxazolidin-2-one (5.69 g, 96%) as a white solid: 1H NMR (CDCl3) δ 2.62 (br s, 3H), 2.91-3.04 (m, 2H), 4.22-4.44 (m, 4H), 4.65-4.73 (m, 1H), 7.22-7.34 (m, 5H), 9.26 (br s, 2H); HPLC ES-MS m/z (rel abundance) 249 (MH+, 100%).

Provenance & Evidence