Hydrochloric Acid → HCID 86643594, compound

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Reaction Steps

(S)-3-(4-Benzyloxy-3-ethylcarbamoyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (220 mg) was dissolved in 4M HCl in dioxane (3 ml) and the solution was left at room temperature for ca 2 hr. Evaporation of solvent gave a white solid which was redissolved in methanol (5 ml) and hydrogenated at 1 atmosphere of hydrogen gas over 5% palladium-carbon (44 mg). After stirring overnight at room temperature the catalyst was removed by filtration and washed with methanol. Evaporation of the filtrate gave a gum which was crystallised from methanol-ether. (S)-2-(3-Ethylcarbamoyloxy-4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as a white solid, 110 mg; NMR (500 MHz, d6 DMSO) 1.07 (3H, t J 7), 2.94-3.09 (4H, m), 3.67 (3H, s), 4.18 (1H, t J 6), 6.84 (3H, br s), 7.56 (1H, t J 5.5), 8.43 (ca 3H, br s), 9.55 (1H, s); HPLC/MS retention time 3.41 min, m/z 283 (MH+).

Provenance & Evidence