4-Methylmorpholine → HCID 86621120, compound

Participants

Reaction Steps

To a solution of the compound of step G (3) (421 mg, 2.69 mmol) and homophenylalanine ethyl ester hydrochloride (789 mg, 3.24 mmol) in DMF (30.1 mL) was added HATU (1.54 g, 3.24 mmol) and N-Methyl morpholine (1.24 mL, 9.42 mmol). The reaction was stirred at rt until LC showed conversion to product (<30 min). DMF was removed in vacuo, the residue suspended in water, and the product extracted 3 times to ethyl acetate. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was suspended in a minimal amount of methylene chloride and filtered through glass wool. The solution was loaded onto a silica gel column, and pure product was obtained following elution with a ethyl acetate/hexane gradient (836 mg, 90%). 1H NMR (500 MHz, CDCl3) δ ppm 0.88 (t, J=7.02 Hz, 3H) 1.19-1.38 (m, 7H) 1.40-1.50 (m, 1H) 1.57-1.69 (m, 1H) 1.92-2.06 (m, 1H) 2.08-2.26 (m, 3H) 2.28-2.41 (m, 1H) 2.52-2.75 (m, 2H) 4.18 (q, J=7.32 Hz, 2H) 4.61-4.74 (m, 1H) 4.95-5.11 (m, 2H) 5.69-5.84 (m, 1H) 5.96 (d, J=7.63 Hz, 1H) 7.10-7.34 (m, 5H). HPLC retention time: 1.76 min (method A). MS (ESI) (M+H)+ 346.

Provenance & Evidence