1-Aminocyclopropane-1-carboxylic acid → 1-{[((2E)-3-Phenylprop-2-enoyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid

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Reaction Steps

Following the general procedure for the one pot synthesis, ACPC (0.4 g, 3.9 mmol) was reacted with chlorotrimethylsilane (0.99 mL, 7.88 mmol) in anhydrous chloroform (10 mL) in the presence of DIEA (1.45 mL, 7.8 mmol). Subsequent reaction of the intermediate with 1-chloroethylchloroformate (0.83 mL, 5.85 mmol) followed by a mixture of DIEA (1.45 mL, 7.8 mmol) and trans-cinnamic acid (1.16 g, 7.88 mmol) provided 0.200 g (16.6% yield) of the title compound (16) as a buff-colored solid after aqueous work-up and mass-guided preparative HPLC purification. M.p: 169.3-172.2° C. 1H NMR (CDCl3, 400 MHz): δ=7.71-7.67 (d, 1H, J=15.6), 7.50 (d, 2H), 7.38 (m, 3H), 6.95 (q, 1H), 6.40 (d, 1H, J=16), 5.58 (s, 0.3H), 5.34 (s, 0.7H), 1.60-1.54 (m, 5H), 1.27-1.24 (m, 2H). MS (ESI) m/z 342.00 (M+Na)+; 318.02 (M−H)−.

Provenance & Evidence