Hydrochloric Acid → HCID 56646839, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-(((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3,5-dimethylphenyl)-5-(3-(6-phenyl-1,4-dioxaspiro[4.5]decan-6-yl)propyl)-1,2,4-oxadiazole (57 mg, 0.101 mmol) in acetic acid (1 mL) was added 1N HCl (0.2 mL, 0.200 mmol), and the mixture was stirred at 0° C. for 1.5 hrs. The mixture was poured into saturated Na2CO3 and the product was extracted with EtOAc (2×). The combined extracts were washed with brine, dried over Na2SO4 and evaporated to give an oily residue. The residue was purified by Combiflash (24 g silica gel) eluting with 1:1 followed by 7:3 EtOAc-hexane, to afford 2-(3-(3-(4-((S)-2,3-dihydroxypropoxy)-3,5-dimethylphenyl)-1,2,4-oxadiazol-5-yl)propyl)-2-phenylcyclohexanone as a solid (34.4 mg). LC/MS: m/e 479.1 (M+H)+. 1H NMR (400 MHz, CCl3D) δ ppm 7.67 (2H, s), 7.31-7.38 (2H, m), 7.24 (1H, t, J=7.25 Hz), 7.14 (2H, d, J=7.47 Hz), 4.06-4.15 (2H, m), 3.75-3.90 (5H, m), 2.70-2.81 (3H, m), 2.26-2.38 (8H, m), 1.84-1.97 (2H, m), 1.59-1.78 (6H, m), 1.37-1.52 (1H, m).

Provenance & Evidence