4-Methylmorpholine → HCID 59428664, compound

Participants

Reaction Steps

To a solution of 0.78 g (2.60 mmol) of (S)-1-(3-methoxy-benzenesulfonyl)-piperidine-2-carboxylic acid and 1.03 g (3.12 mmol) of (S)-2-amino-3-(1-indol-3-yl)-naphthalen-2-yl-propionamide in dichloromethane (100 ml) was added 0.16 g (1.30 mmol) DMAP followed by addition of 4-methylmorpholine 1.37 g (13.54 mmol), HOBT 0.84 g (6.25 mmol) and EDCI 1.39 g (7.29 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was then washed with water, dried (sodium sulfate). Chromatography on silica gel eluting with 50% ethyl acetate/heptane proved 1.2 g (1.96 mmol) of the title compound. 1H NMR (300 MHz, CDCl3): 1.34-1.01 (m, 5H); 2.07 (bd, 1H); 2.21 (dd, 1H); 3.43-3.48 (m, 3H); 3.83 (s, 3H); 4.34 (b, 1H); 4.98 (q, 1H); 6.98 (d, 1H); 7.09-7.47 (m, 11H); 7.68-7.80 (m, 4H); 8.15 (s, 1H); 8.21 (s, 1H); 8.40 (s, 1H).

Provenance & Evidence