L-Glutamine → Tris(2-aminoethyl)amine

Participants

Reaction Steps

Approximately 140 mg of Pearlman's catalyst was added to a solution of compound 3-1 (1.2 mmol) in ethyl acetate (50 mL). The reaction mixture was placed under 50 psi of hydrogen for 1.5 hours. The catalyst was removed by filtration through Celite, and the solvent was removed. A solution of the debenzoylated, lipidic amino acid (1.2 mmol) and tris(2-aminoethyl)amine (0.31 mmol) was prepared in dichloromethane (12 mL). N-Hydroxybenzotriazole (1 mmol) and dicyclohexylcarbodiimide (1 mmol) were added in succession, and the reaction proceeded at room temperature for 24 hours. Dichloromethane was added, and the organic solution was washed with saturated sodium bicarbonate and brine, and dried with anhydrous magnesium sulfate. The product was purified by chromatography on silica gel (5% methanol in dichloromethane) producing 326 mg (45% yield). 1H NMR (300 MHz, CDCl3, TMS=0) d 6.98 (bs, 3H), 5.67 (bd, 3H) 4.50 (m, 3H), 3.60-3.00 (m, 20H), 2.62 (bs, 6H), 2.29 (m, 6H), 2.00-1.40 (m, 22H), 1.42 (s, 18H), 1.25 (bs,190H), 0.88 (t, 18H, J=6.9).

Provenance & Evidence