4-Methylmorpholine → HCID 59708027, compound

Participants

Reaction Steps

To a solution of [1S-(1α, 2α, 3α, 4α)]-2-[[3-Carboxy-7-oxabicyclo[2.2.1]hept-2-yl]methyl]-4-fluoro-1-phenylmethoxybenzene (0.3 g, 0.825 mmol), N-(4-cyclohexyl)butyl)-L-serinamide (0.2 g, 0.825 mmol), HBOt (0.122 g, 0.91 mmol), 4-methylmorpholine (0.1 mL, 0.91 mmol) in dimethylformamide (5 mL), at 0° C. and under nitrogen atmosphere, was added portion-wise EDAC (0.174 g, 0.91 mmol). The resulting mixture was stirred for 10 minutes then it was allowed to warm slowly to room temperature and stirred for 16 h. After this time, the reaction was stopped and the solvent was evaporated under vacuum. The crude material was partitioned between ethyl acetate (15 mL) and 2M HCl (10 mL). The organic phase was separated; it was washed with a sat. solution of sodium bicarbonate (10 mL), Brine (10 mL), dried (MgSO4), filtered and the solvent evaporated “under vacuum” to give the titled product as an oil which was used in the next step without any additional purification. 1H-NMR (CDCl3, 300 MHz) δ 7.30 (m, 5H, ArH), 7.03 (t, 1H, J=5.8 Hz, CONH), 6.80 (m, 4H, ArH+NH), 5.03 (s, 2H, —OCH2Ph), 4.69 (d, 1H, J=5.1 Hz, —CH—O—), 4.42 (m, 1H, —CONHCHCO—), 4.33 (d, 1H, J=5.1 Hz, —CH—O—), 3.97 (dd, 1H, J=3.8, 11.3 Hz, —CH2OH), 3.56 (dd, 1H, J=5.5, 11.3 Hz, —CH2OH), 3.12 (m, 2H, —NCH2—), 2.73-2.40 (m, 4H, —CH—+—CH2—), 1.63-0.70 (m, 21H, —CH2—CH2—)

Provenance & Evidence