Diisopropylethylamine → HCID 68669056, compound

Participants

Reaction Steps

A solution of 2-(4-butyl-2,3-dioxopiperazin-1-yl)acetic acid (Intermediate F, 142 mg, 0.62 mmol), (R)-2-tert-butoxycarbonylamino-2-benzylpropanehydrazide (Intermediate B, 225 mg, 0.77 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (131 mg, 0.68 mmol), 1-hydroxy-7-azabenzotriazole (93 mg, 0.68 mmol) and diisopropylethylamine (0.12 mL, 0.68 mmol) in 6.2 mL DMF was stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water and brine. Drying, solvent evaporation and flash chromatography (silica gel, 0-10% MeOH/CH2Cl2) gave 1-((2-((R)-2-tert-butoxycarbonylamino-2-methyl-3-phenylpropanoyl)hydrazino)acetyl)-4-butylpiperazine-2,3-dione. 1H NMR (CDCl3) δ 7.26 (m, 3H), 7.17 (m, 2H), 4.25 (A of AB, 1H, J=15.9 Hz), 4.20 (B of AB, 1H, J=15.6 Hz), 3.74 (m, 1H), 3.62 (m, 3H), 3.47 (m, 3H), 3.08 (m, 1H), 1.57 (m, 2H), 1.46 (s, 9H), 1.40 (s, 3H), 1.36 (m, 2H), 0.94 (t, 3H, J=7.2 Hz).

Provenance & Evidence