Ammonia → HCID 18442917, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(methoxycarbonyl)-3-[4-[2-(5,6,7,8-tetrahydro-2-naphthoxy)ethoxy]phenyl]propionic acid (2.10 g, 5.29 mmol) in benzene (20 ml) at room temperature is added thionyl chloride (0.76 g, 6.34 mmol). Then the mixture was heated at 80° C. for 90 min. After cooled to rooms temperature, the solvent is removed under a vacuum. To the residue is added 28% ammonia solution (5.49 ml, 79.30 mmol) at room temperature. The mixture is stirred for 30 min, dissolved in ethyl acetate (20 ml), washed with brine (3×15 ml), dried over sodium sulfate, and concentrated. The crude product is crystallized from ethanol to give title compound (1.09 g, 52%). HRMS calcd for C23H27NO5: 397.4711. Found: 397.4713. MA calcd for C23H27NO5: C, 69.50%; H, 6.85%; N, 3.52%. Found: C, 69.62%; H, 6.83%; N, 3.53%.

Provenance & Evidence