Benzyl Chloride → HCID 86643599, compound

Participants

Reaction Steps

(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-methylcarbamoyloxy-phenyl)-propionic acid methyl ester (427 mg) was dissolved in methanol (40 ml) containing 5% Pd—C (46 mg) and benzyl chloride (140 mg). The mixture was stirred under an atmosphere of hydrogen for 4 hours. The catalyst was removed by filtration and washed with methanol. The filtrate was evaporated to dryness giving a gum which was triturated with ether. (S)-2-(4-Hydroxy-3-methylcarbamoyloxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as a white solid, 239 mg; NMR (500 MHz, d6 DMSO) 2.64 (ca 3H, d J 5), 2.97 (1H, dd J 14.5, 7), 3.04 (1H, dd J 14.5, 6), 3.67 (3H, s), 4.19 (1H, t J 6.5), 6.82-6.88 (3H, m), 7.44 (1H, q J 5 s exch D2O), 8.52 (3H, br s exch D2O), 9.57 (1H, s, exch D2O); HPLC/MS retention time 3.04 min, m/z 309 (MH+).

Provenance & Evidence