Potassium Carbonate → (R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(2-ethoxyethoxy)phenyl)propanoate

Participants

Reaction Steps

To a suspension of (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)-propanoate (4.43 g, 15.00 mmol), K2CO3 (4.15 g, 30.0 mmol) and sodium iodide (112 mg, 750 μmol) in acetonitrile (100 mL) was added 1-bromo-2-methoxyethane (5.64 mL, 60.0 mmol) and the resulting mixture was stirred at reflux for 2 days. The reaction mixture was diluted with TBME and washed with H2O and brine. Combined extracts were dried over MgSO4, filtered and concentrated to provide the title compound as a yellow oil (5.3 g, 95%). TLC (toluene/TBME 2:1) Rf=0.44; tR=1.084 min (UPLC 1); LC-MS: [M+H] 354; Rt 1.02 min; (LCMS method 2); 1H NMR (400 MHz, CDCl3): δ 7.05 (d, 2H), 6.88 (d, 2H), 4.96 (br d, 1H), 4.58 (m, 1H), 4.12 (dd, 2H), 3.76 (dd, 2H), 3.73 (s, 3H), 3.47 (s, 3H), 3.05 (m, 2H), 1.44 (s, 9H).

Provenance & Evidence