Dicyclohexylcarbodiimide → HCID 11363567, compound

Participants

Reaction Steps

To a solution of Fmoc-β-Ala-OH (311 mg, 1.0 mmol) and PfpOH(334 mg, 1.75 mmol) in DMF (2.5 mL) was added DCC (288 mg, 1.4 mmol) at 0° C. for 30 min and then room temperature for 15 h. The reaction mixture was filterd to remove DCUrea, the flitrate was evaporated in vacuo, and the residue was flush-chromatographed (CH2Cl2). The crude Fmoc-β-Ala-OPfp was recrystallized using hexane and CH2Cl2 to give the pure Fmoc-β-Ala-OPfp (429 mg 90%) as a white powder. To a solution of Fmoc-β-Ala-OPfp (100 mg, 0.21 mmol) and BocPNA-OH (41 mg, 0.19 mmol) in DMF (2 mL) was added diisoprppylethylamine (36 il, 0.21 mmol) and the reaction mixture was stirred at room temperature for 15 h. The reaction mixture was evaporated in vacuo and the residue was flush-chromatographed (0-10% MeOH/CH2Cl2) to give Fmoc-Gly-BocPNA-OH (41 mg, 42%). 1H NMR (DMSO-d6) δ 7.88 (d, J=7.4 Hz, 2H), 7.68 (d, J=7.4 Hz, 2H), 7.41 (t, J=7.3 Hz, 2H), 7.33 (t, J=7.3 Hz, 2H), 7.18 (m, 2H), 6.83 (brt) and 6.72 (brt) (2H), 4.3-4.2 (m, 4H), 4.05-3.9 (m, 3H), 3.33 (brt) and 3.29 (brt) (2H), 3.19 (m, 2H), 3.07 (brq) and 3.02 (brq) (2H), 1.36 (brs, 9H) ; 13C NMR (DMSO-d6) δ 171.20 (d), 170.85 (d), 155.93, 155.56, 143.87, 140.69, 127.55, 127.01, 125.09, 120.05, 77.73 (d), 65.30 (d), 59.69, 47.35 (d), 46.68, 46.49 (d), 37.99 (d), 36.72 (d), 28.14 (d).

Provenance & Evidence