Sodium Hydroxide → (R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid

Participants

Reaction Steps

A solution of (R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid benzyl ester (1.43 g, 2.52 mmol) in methanol (15 ml) is treated with NaOH solution, (2.5 ml, 4M). The reaction mixture is stirred at ambient temperature for 1 hour. The methanol is evaporated and the resulting aqueous solution diluted with water and washed with diethyl ether. The aqueous phase is neutralised with 1N HCl solution and extracted into isopropanol/chloroform (1:3). The organic phase is evaporated and dried under high vacuum to afford (R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid. [MH]+ 482.1.

Provenance & Evidence