1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69686698, compound

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Reaction Steps

A suspension of 5-(N′-benzyloxycarbonyl-N-tert-butoxycarbonylmethyl-hydrazino)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-oxo-pentanoic acid benzyl ester (3) and 10% palladium on carbon (250 mg) in tetrahydrofuran (THF) (30 mL) and DMF (3 mL) was stirred under hydrogen atmosphere for 16 hours. The mixture was filtered through Celite and the filtrate was evaporated in vacuo. The residue was dissolved in 30 mL of dichloromethane. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (770 mg, 4 mmol) was added and the solution was stirred at room temperature for 3.5 hours. Solvent was removed in vacuo and the residue was dissolved in ethyl acetate (300 mL), then washed with water (100 mL×2). The organic layer was dried over anhydrous Na2SO4, filtered, purified by flash chromatography using hexane/ethyl acetate (85/15 to 50/50) to afford 1.06 g (75% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.40 (s, 9H), 2.30-2.40 (m, 1H), 2.40-2.50 (m, 1H), 3.05-3.12 (m, 1H), 3.38-3.48 (m, 1 H), 3.90-4.00 (d, 1H), 4.60-4.70 (d, 1H), 5.55-5.63 (m, 1H), 7.65 (s, 1H), 7.75-7.7.9 (m, 2H), 7.88-7.92 (m, 2H). Analytical HPLC: 10.36 min. LC-MS (ES+): m/e=388 (M+H+).

Provenance & Evidence