Benzyl Chloride → HCID 86643606, compound

Participants

Reaction Steps

(S)-2-[(S)-2-Benzyloxycarbonylamino-3-(3,4-bis-benzyloxy-phenyl)-propionylamino]-3-(3-benzyloxy-4-methylcarbamoyloxy-phenyl)-propionic acid methyl ester (0.40 g, 0.470 mmol) was suspended in ethyl acetate (20 ml) and methanol (20 ml). Pd/C (5%, 0.10 g) and benzyl chloride (0.065 g, 0.517 mmol) were added. The hydrogenation was carried out under 30 psi of hydrogen for 3 h. After filtration and removal of solvent, the residue was redissolved in methanol (2 ml). Diethyl ether was added and a white solid precipitated. (S)-2-(3,4-Dihydroxy-phenyl)-1-[(S)-2-(3-hydroxy-4-methylcarbam-oyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-ethyl-ammonium chloride was obtained as a white solid by filtration, 0.22 g. 1H NMR (400 MHz, d6-DMSO) 2.63 (d, 3H), 2.72 (m, 1H), 2.83-3.02 (m, 3H), 3.64 (s, 3H), 3.93 (m, 1H), 4.50 (m, 1H), 6.52 (m, 1H), 6.65 (m, 3H), 6.85 (m, 2H), 7.46 (m, 1H), 8.11 (s, 3H), 8.87 (s, 1H), 8.96 (s, 1H), 9.13 (m, 1H), 9.61 (s, 1H). m/z 448 (MH+).

Provenance & Evidence