Benzyl Chloride → HCID 86643595, compound

Participants

Reaction Steps

(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-dimethylsulfamoyloxy-phenyl)-propionic acid methyl ester (615 mg) was dissolved in methanol (30 ml) containing benzyl chloride (180 mg) and 5% palladium-carbon (60 mg). The mixture was stirred overnight under an atmosphere of hydrogen gas. The catalyst was removed by filtration and washed with methanol. Evaporation of the filtrate gave a gum which was crystallised by trituration with ether. (S)-2-(3-Dimethylsulfamoyloxy-4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as an off-white solid, 320 mg; NMR (500 MHz, d6 DMSO) 2.89 (3H, s), 2.97 (1H, dd J 14, 8), 3.01-3.08 (4H, m), 3.67 (3H, s), 4.19 (1H, t J 7), 6.84-6.88 (3H, m), 8.54 (ca 3H, br exch D2O), 9.58 (1H, s, exch D2O); HPLC/MS retention time 2.68 min, m/z 283 (MH+).

Provenance & Evidence