1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,4-bis(nitrooxy)butyl (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate

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Reaction Steps

To a solution of 1.72 g of (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 30 mL of CH2Cl2 at 0° C. was added 750 mg of 3,4-bis(nitrooxy)butyl alcohol, 560 mg of DMAP and 880 mg of EDCI. The mixture was stirred at RT for 2 h then quenched by addition of NH4Cl sat., extracted with EtOAc, washed with NaHCO3 sat., brine and dried over sodium sulfate. Purification by flash chromatography afforded 930 mg of the titled compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 7.77 (d, 2H), 7.43 (d, 2H), 7.17-7.15 (m, 3H), 7.08 (dd, 2H), 5.56-5.52 (m, 1H), 5.22 (s, 2H), 4.95 (dd, 1H), 4.69 (dd, 1H), 4.47-4.41 (m, 2H), 3.05 (s, 3H), 2.32-2.19 (m, 2H), 1.89 (s, 3H).

Provenance & Evidence