4-Methylmorpholine → HCID 13072333, compound

Participants

Reaction Steps

To a -10° C. solution of Cbz-Asp(O-t-Bu) (2.5 g, 4.95 mmol) in THF (40 mL) were added NMM (0.52 g, 5.18 mmol) followed by isobutylchloroformate (0.705 g, 5.16 mmol) to form a white precipitate. The suspension was stirred for 4 minutes and a solution of Phe-NH2 (0.81 g, 4.94 mmol) in DMF (10 mL) and water (5 mL) were added. The solution was stirred at -15° C. for additional 10 minutes then allowed to warm to ambient temperature. After 6 hours, the solution was diluted with ethyl acetate, washed with 1M HCl, saturated bicarbonate solution and brine. After drying over anhydrous sodium sulfate, the solvent was removed in vacuo to yield 2.07 g (89% yield) of the title compound as a white solid which was recrystallied from ethyl acetate. MS(FAB+) m/e 470 (M+H+). 1H NMR (300 MHz,CDCl3) δ1.41 (s, 9H), 2.67 (dd, J=6 and 15 Hz, 1H), 2.80 (dd, 1H), 3.03-3.22 (m, 2H), 4.42 (m, 2H), 4.64 (m, 2H), 5.17 (dd, 2H), 7.15-7.40 (m, 10H).

Provenance & Evidence