4-Methylmorpholine → HCID 178512239, compound

Participants

Reaction Steps

[(S)-2-Phenyl-1-(3-pyrrolidin-1-yl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester. To a mixture of EDCl (5.75 g, 30 mmol), HOBT (4.05 g, 30 mmol) and (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid (5.3 g, 20 mmol) in DMF (80 mL), was added 3-pyrrolidin-1-yl-propylamine (3.85 g, 30 mmol) in DMF (10 mL) followed by N-methylmorpholine (4.05 g, 40 mmol) in 10 mL of DMF at rt. The solution was stirred for 14 h and was diluted with ethyl acetate (500 mL). The organic layer was washed with saturated NaHCO3 (2×100 mL), brine (3×100 mL) and dried (Na2SO4). The solvent was removed, and the crude residue was stirred in a mixture of 10% EtOAc/hexanes for 1 h to afford 6.5 g (87%) of the desired product as a white solid. MS (electrospray): mass calculated for C21H33N3O3, 375.25, m/z found, 376.2 [M+H]+, 398.2 [M+Na]+. 1H NMR (400 MHz, CD3OD): 7.25–7.18 (m, 5H), 4.22 (t, J=3.6 Hz, 1H), 3.18–3.14 (m, 2H), 3.04 (dd, J=22.0, 6.5 Hz, 1H), 2.83 (dd, J=22.0, 8.3 Hz, 1H), 2.53–2.49 (m, 4H), 2.42 (t, J=7.9 Hz, 1H), 1.81–1.76 (m, 4H), 1.65–1.61 (m, 2H), 1.37 (s, 9H).

Provenance & Evidence