Hydrochloric Acid → HCID 178508116, Verbindung
Reaktionsgleichung
Cl.C([O:6][C:7]([C@:9]1([NH:28]C(OC(C)(C)C)=O)[CH2:14][C@H:13]([S:15][C:16]2[N:20]=[CH:19][NH:18][N:17]=2)[C@@H:12]2[C@H:10]1[C@H:11]2[C:21]([O:23]C(C)(C)C)=[O:22])=[O:8])(C)(C)C>O1CCOCC1>[NH2:28][C@@:9]1([C:7]([OH:8])=[O:6])[CH2:14][C@H:13]([S:15][C:16]2[N:20]=[CH:19][NH:18][N:17]=2)[C@@H:12]2[C@H:10]1[C@H:11]2[C:21]([OH:23])=[O:22]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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).