1-Aminocyclopropane-1-carboxylic acid → 1-[(Cyclohexylcarbonyloxyethoxy)carbonylamino]cyclopropanecarboxylic Acid

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Reaction Steps

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (426 mg, 4.2 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl cyclohexanecarboxylate (1.1 g, 3.5 mmol) were reacted to provide 172 mg (16% yield) of the title compound (10) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 123.6-125.3° C. 1H NMR (CDCl3, 400 MHz): δ=9.92 (br s, 1H), 6.76 (q, 1H), 6.34 (br s, 0.3H), 5.59 (s, 0.7H), 2.27 (m, 1H), 1.10-1.95 (m, 17H). MS (ESI) nm/z 317.15 (M+NH4)+; 322.13 (M+Na)+; 298.15 (M−H)−.

Provenance & Evidence