Cesium carbonate → (S)-4-(Dimethylamino)-4-oxo-3-(4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methoxy)phenyl)butanoic acid

참여 물질

반응 단계

The phenol 22.2 (315 mg, 1.26 mmol) is dissolved in 5 mL of DMF and 6-bromomethyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene (available from Maybridge) (1.38 mmol) is added followed by cesium carbonate (600 mg, 1.88 mmol). The reaction is stirred for 14 hours and diluted with 250 mL of EtOAc. The organic layer is washed with 1N HCl (aq) (50 mL), saturated NaHCO3 (aq) (50 mL), and brine (2×50 mL). The organic layer is dried with MgSO4, filtered, and concentrated under reduced pressure. The residue is dissolved in 15 mL THF and 0.111 N NaOH (aq) (16 mL, 1.78 mmol) and MeOH (10 mL) is added. The solution is stirred for 8 hours and concentrated to remove the organic solvent. The slurry is diluted with water (50 mL) and DCM (300 mL). The mixture is adjusted with 2 N HCl (aq) to a pH of 2 and then extracted with DCM (3×75 mL). The combined organic layers are dried with Na2SO4 and concentrated under reduced pressure. The residue is purified by flash chromatography to yield compound 22.

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