1,1'-Carbonyldiimidazole → HCID 10416128, compound

Participants

Reaction Conditions

Reaction Steps

Carbonyldiimidazole (CDI, 0.592 g, 3.65 mmol) was added to (8) (1.42 g, 3.48 mmol) in dry CH2Cl2 (90 mL) . After stirring for 1 hour, the solution was cooled to 0° C. and (6) (free amine, 0.74 g, 3.55 mmol) in CH2Cl2 (65 mL) was added by cannula over 5 minutes. After stirring for 12 hours (0° C. to room temperature), solvent was removed by rotary evaporation. Dilute brine (200 mL) was added, followed by extraction with EtOAc (4×100 mL). The organic phase was washed with 100 mL portions of cold 0.5M citric acid, 5% NaHCO3 and brine. Solvent removal led to 2.2 g (quantitative) of (9) as an oil, which was used directly in the next step. An analytical sample was chromatographed on silica gel, eluting with 3.5% EtOH/CHCl3 : 300 MHz NMR δ 1.1-1.7 (m+s, 21 H), 2.3-3.3 (m, 10 H), 3.60 (t, 2 H, J=7), 4.6 (br s, 1 H), 4.67 (s, 2 H), 4.80 (s, 2 H), 6.0 (br s, 1 H), 7.25-7.40 (m, 10 H). Anal. calcd. for C33H50N4O6 : C, 66.19; H, 8.42; N, 9.36. Found: C, 66.27; H, 8.40; N, 9.33.

Provenance & Evidence