Diethyl Ether → HCID 86643596, compound

Participants

Reaction Steps

[(S)-2-(4-Benzyloxy-3-ethylcarbamoyloxy-phenyl)-1-methylcarbamoyl-ethyl]-carbamic acid tert-butyl ester (243 mg) was suspended in 4M HCl-dioxane (5 ml) and stirred at room temperature for 1 hour. The clear solution was evaporated to dryness giving an oil which was redissolved in methanol (5 ml). 5% Pd—C (50 mg) was added and the mixture stirred under an atmosphere of hydrogen gas at room temperature for 2 hours. The catalyst was removed by filtration and washed with methanol. Evaporation of the filtrate gave the crude product as an oil. Trituration with ether gave (S)-2-(3-ethylcarbamoyloxy-4-hydroxy-phenyl)-1-methylcarbamoyl-ethyl-ammonium chloride as a grey solid, 150 mg; NMR (500 MHz, d6 DMSO) 1.07 (3H, t J 7), 2.59 (3H, d J 4.5 collapse to s with D2O), 2.82-2.95 (2H, m), 3.03-3.10 (2H, m), 3.83 (1H, t J 7), 6.81-6.85 (3H, m), 7.55 (1H, t J 5.5), 8.19 (3H, br exch D2O), 8.37 (1H, br q exch D2O), 9.5 (1H, s, exch D2O); HPLC/MS Retention time 2.9 min, m/z 282 (MH+).

Provenance & Evidence