Triethylamine → HCID 178454265, compound

Participants

Reaction Steps

A solution of N-α-Boc-L-lysine 18 (5.00 g, 20.3 mmol) in CH2Cl2 (100 mL) was charged with N,N′-bis-Boc-1-guanylpyrazole (5.10 g, 16.6 mmol) and triethylamine (5.54 mL, 40.6 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was washed with 10% aqueous citric acid (2×80 mL) and the solvent was removed under reduced pressure. The residue was dissolved in 1 N NaOH (200 mL), the pH of solution was adjusted to 5-6 with 1 N HCl, and the mixture was extracted with CH2Cl2 (300 ml). The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (2×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford compound 10 (9.00 g, 91%) as a white solid: 1H NMR (400 MHz, CD3OD) δ 4.10-4.02 (m, 1H), 3.36 (t, J=6.8 Hz, 2H), 1.90-1.78 (m, 1H), 1.73-1.56 (m, 3H), 1.52 (s, 9H), 1.45-1.31 (m, 2H), 1.47 (s, 9H), 1.43 (s, 9H).

Provenance & Evidence