Hydrochloric Acid → HCID 71695828, compound

Participants

Reaction Conditions

Reaction Steps

Charge a 5 mL ReactiVial with ditert-butyl (1S,2S,5R,6S)-2-(tert-butoxycarbonylamino)spiro[bicyclo[3.1.0]hexane-4,1′-cyclopropane]-2,6-dicarboxylate (55 mg, 129.8 μmol). To this add a 5N aqueous hydrochloric acid solution (3 mL; 20.8 mmol) and 1,4-dioxane (1 mL). Stir the mixture at 90° C. for one hour. Seal the ReactiVial and continue stirring at 90° C. for 3 hours. Cool to ambient temperature and stand for 3 days. Concentrate under reduced pressure to a dark solid. Prepare a Oasis® HLB Waters (1 g) cartridge by washing with 2 column volumes of methanol, followed by 6 column volumes of water. Dissolve the dark solid in water and load onto the cartridge. Wash the cartridge with water (2 column volumes) and collect the eluent. Freeze-dry the solution to yield title compound (16.1 mg, 65 μmol). MS (m/z): 212 (M+1). 1H NMR (D2O) δ 0.45 (m, 1H), 0.53 (m, 1H), 0.64 (m, 1H), 0.74 (m, 1H), 1.72-1.78 (m, 2H) 1.86 (d, J=14.2 Hz, 1H), 2.07 (m, 1H), 2.37 (m, 1H).

Provenance & Evidence