1-Aminocyclopropane-1-carboxylic acid → 1-{[(3,4-Dimethoxyphenylcarbonyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid

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Reaction Steps

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (0.122 g, 1.21 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 3,4-dimethoxybenzoate (0.4 g, 1.01 mmol) were reacted to provide 0.260 g (68% yield) of the title compound (14) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 171.8-173.6° C. 1H NMR (CDCl3, 400 MHz): δ=7.69 (d, 1H), 7.47 (s, 1H), 7.13 (d, 1H), 6.83 (d, 1H), 5.52 (s, 0.3H), 5.43 (s, 0.7H), 3.98 (d, 6H), 1.62 (m, 5H), 1.31 (br s, 2H). MS (ESI) m/z 375.99 (M+Na)+; 352.02 (M−H)−.

Provenance & Evidence