Triethylamine → HCID 178454264, compound

Participants

Reaction Steps

A solution of N-α-Boc-D-lysine 12 (10.0 g, 40.6 mmol) in CH2Cl2 (200 mL) was charged with N,N′-bis-Boc-1-guanylpyrazole (11.3 g, 36.6 mmol) and triethylamine (11.0 mL, 81.3 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was washed with 10% aqueous citric acid (2×100 mL) and the solvent was removed under reduced pressure. The residue was dissolved in 1 N NaOH (300 mL), 1 N HCl was added to adjust the pH to 5-6, and the mixture was extracted with CH2Cl2 (500 ml). The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (2×250 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford compound 8 (18.5 g, 94%) as a white solid: 1H NMR (400 MHz, CD3OD) δ 4.13-4.03 (m, 1H), 3.36 (t, J=6.8 Hz, 2H), 1.91-1.77 (m, 1H), 1.74-1.55 (m, 3H), 1.52 (s, 9H), 1.51-1.38 (m, 2H), 1.47 (s, 9H), 1.43 (s, 9H).

Provenance & Evidence