Hydrochloric Acid → HCID 23147524, compound

Participants

Reaction Steps

In the same manner as in the step 1 in Example 317, 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3-(2-tetrahydropyran-2-yloxyethyl)-3H-1,3,4-oxadiazol-2-one was obtained from 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3H-1,3,4-oxadiazol-2-one (280 mg, 0.57 mmol) obtained in the step 2 in Example 315, using potassium carbonate (200 ng, 1.4 mmol), 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.13 mL, 0.86 mmol) and N,N-dimethylformamide (3.0 mL). The resulting 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3-(2-tetrahydropyran-2-yloxyethyl)-3H-1,3,4-oxadiazol-2-one was dissolved in methanol (3.0 mL), and methanol solution (2.0 mL) of 10% hydrogen chloride was added thereto and stirred at room temperature for 30 minutes. The reaction solution was neutralized with aqueous saturated sodium hydrogencarbonate solution added thereto, and then extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/1 to 1/0) to obtain 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3-(2-hydroxyethyl)-3H-1,3,4-oxadiazol-2-one (260 mg, 85%).

Provenance & Evidence