Acetic Anhydride → HCID 11051114, compound

Participants

Reaction Steps

6,17,28-Tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile (13) was prepared by dissolving compound (12) (1.1 g, 1.4 mmol) in pyridine (16 mL), adding acetic anhydride (4 mL) and stirring the solution for 12 hours. After removal of solvents under high vacuum, water was added, followed by extraction with CHCl3. The organic extracts were washed with 1N HCl and saturated NaHCO3. Column chromatography (5% CH3OH/CHCl3) gave 1.05 g (91%) of (13): NMR δ 1.4-1.59 (m, 4 H), 1.59-1.70 (m, 6 H), 1.70-1.85 (m, 6 H), 2.1 (s, 3 H), 2.35 (t, 2 H), 2.40-2.55 (m, 4 H), 2.75-2.90 (m, 4 H), 3.18-3.28 (m, 4 H), 3.6-3.7 (m, 6 H), 4.8 (s, 2 H), 4.82 (s, 2 H), 4.84 (s, 2 H), 6.20-6.75 (m, 2 H), 7.4 (s, 15 H). Anal. calcd. for C46H62N6O8 : C, 66.30; H, 7.68. Found: C, 66.44; H, 7.66 [Bergeron at al, J. Org. Chem., supra].

Provenance & Evidence