Diethyl [(3-azidopropane-1-sulfonyl)amino]propanedioate → Diethyl [(3-aminopropane-1-sulfonyl)amino]propanedioate

Participants

Reaction Steps

A solution of 3-azidopropanesulfonamidomalonate diethyl ester (27.60 g, 0.086 mol,) in ethanol (70 mL) and 1 g of Pd/C (10%) were placed in a Parr hydrogenation apparatus under 60 psi H2 for 8 hours. The hydrogen was replenished every 2 hours. The mixture was filtered through a pad of Celite and a solution of 1 N HCl in ethanol (10 mL) was added to the filtrate. The solvent was removed in vacuo and the residue was purified by column chromatography on Al2O3 using CH2Cl2/MeOH (4/1, v/v) to give 26.84 g of the title compound as the hydrochloride salt: 1H NMR (CDCl3) δ 1.30 (t, 6, CH3), 2.12 (m, 2, OCH2CH3), 3.21 (t, 2, CH2), 3.50 (t, 2, CH2), 4.26 (m, 4, OCH2CH3), 4.84 (d,1, CH), 6.09 (d, 1, NH), 8.29 (br.s, 2, NH3). 13C NMR (CDCl3) 613.6, 26.3, 42.5, 51.2, 58.5, 62.7, 165.9.

Provenance & Evidence