Triethylamine → HCID 68725422, compound

Participants

Reaction Steps

(S)-2-(3-Benzyloxy-4-methylcarbamoyloxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was suspended in dichloromethane (20 ml), then triethylamine (0.18 g) was added, followed by the addition of (S)-2-benzyloxycarbonylamino-3-(3,4-bis-benzyloxy-phenyl)-propionic acid (0.85 g), [see German patent DE 2121187], and HOBt (0.25 g). The mixture was stirred at room temperature for 20 min. EDC (0.35 g) was added and stirring was continued overnight. The mixture was washed with sodium bicarbonate, dried over sodium sulfate. After removal of the solvent, the residue was purified by silica gel chromatography eluting with ethyl acetate/dichloromethane (1:2). (S)-2-[(S)-2-Benzyloxycarbonylamino-3-(3,4-bis-benzyloxy-phenyl)-propionylamino]-3-(3-benzyloxy-4-methylcarbamoyloxy-phenyl)-propionic acid methyl ester was obtained as a white solid, 1.25 g. 1H NMR (400 MHz, CDCl3) 2.63 (d, J=4.6 Hz, 3H), 2.87-3.06 (m, 4H), 3.56 (s, 3H), 4.28-4.34 (m, 1H), 4.53-4.58 (m, 1H), 4.86-5.09 (m, 8H), 6.78 (m, 2H), 6.95 (m, 2H), 7.09 (m, 2H), 7.20-7.54 (m, 22H), 8.51 (m, 1H).

Provenance & Evidence