Hydrochloric Acid → HCID 178508116, compound

Participants

Reaction Steps

Add 4M hydrogen chloride in 1,4-dioxane (20 mL) to a solution of ditert-butyl(1R,2S,4S,5R,6R)-2-tert-butoxycarbonylamino-4-(1H-[1,2,4]triazol-3-ylsulfanyl)-bicyclo[3.1.0]hexane-2,6-dicarboxylate (1.64 g, 3.30 mmol) in 1,4-dioxane (20 mL) and shake mixture at 50° C. overnight. Concentrate to dryness. Purify by cationic ion exchange (DOWEX® Marathon C, Na+ Form strongly acidic). Dissolve the residue in a minimum amount of water to solubilize the material and load onto the resin. Wash the resin successively with 2 column volume of water, then 2 column volume of water: tetrahydrofuran (1:1) and 2 column volumes of water. Elute the desired product with 2 column volumes of 10% pyridine in water to give the title compound as a white solid. MS (m/z): 285 (M+1). 1H NMR (300 MHz, D2O): 4.25 (d, J=7.3 Hz, 1H), 2.53-2.38 (m, 3H), 2.23 (dd, J=8.1, 16.1 Hz, 1H), 1.95 (t, J=3.3 Hz, 1H).

Provenance & Evidence