ethyl 3-(benzhydrylamino)propanoate

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl acrylate (1.05 g; 10.0 mmol) and diphenylmethyamine (1.83 g; 10.0 mmol) were dissolved in absolute ethanol (25 mL) and stirred overnight at 70° C. The solution was evaporated and crude ethyl 3-(diphenylmethylamino)propionate (2.85 g; 10.0 mmol) was dissolved in DMF (50 mL). 4-Methoxybenzenesulfonyl chloride (2.30 g; 11.0 mmol) and pyridine (10 mL) were added and the mixture stirred overnight at 70° C. The dark reaction was washed with 1 N HCl (2×100 mL). The combined extracts were washed with saturated aqueous NaCl (100 mL), dried over MgSO4, filtered, and evaporated to an oil. The black residue was eluted through a filter pad of silica gel using a hexanes/ethyl acetate step gradient to remove polar material. Preparative HPLC purification, eluting with a mixture of ethyl acetate/hexanes (35:65), gave 1.06 g (23%) of the title compound as a pale yellow oil. 300 MHz 1H-NMR (CDCl3): δ 1.16 (t, 3H), 2.12 (m, 2H), 3.57 (m, 2H), 3.84 (s, 3H), 3.99 (q, 2H), 6.48 (s, 1H), 6.83 (d, 2H), 7.04 (m, 4H), 7.24 (m, 6H), 7.64 (d, 2H). The solution was evaporated the mixture stirred overnight at 70° C The dark reaction was washed with 1 N HCl (2×100 mL) The combined extracts were washed with saturated aqueous NaCl (100 mL) dried over MgSO4 filtered evaporated to an oil The black residue was eluted through a filter pad of silica gel using a hexanes/ethyl acetate step gradient to remove polar material Preparative HPLC purification eluting with a mixture of ethyl acetate/hexanes (35:65)