Succinic anhydride → 5,16-Bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid

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Reaction Steps

5,16-Bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid (10 ) was prepared by heating a solution of (9) (0.365 g, 0.738 mmol) and succinic anhydride (0.113 g, 1.13 mmol) in pyridine (10 mL) at 106° C. for 1.5 hours under N2. After removing the pyridine in vacuo, the residue was diluted with ether (25 mL) and then extracted with saturated NaHCO3 (3×25 mL). The combined aqueous portion was extracted further with ether (2×25 mL), then cautiously acidified with cold 6 N HCl (20 mL). Extraction with CHCl3 (3×40 mL), followed by a final water wash (40 mL) and solvent removal led to 0.424 g of (10) (96% yield): NMR δ 1.25-1.84 (m, 10 H), 2.2-2.92 (m, 10 H), 3.05-3.33 (m, 2 H), 3.5-3.8 (m, 4 H), 4.80 and 4.83 (2 s, 4 H), 6.6 (br s, 1 H), 7.34 (s, 10 H). Anal. calcd. for C32H42N4O7 : C, 64.63; H, 7.12; N, 9.42. Found: C, 64.70; H, 7.16; N, 9.39.

Provenance & Evidence