Sodium Hydroxide → HCID 11784106, compound

Participants

Reaction Steps

To a solution of 46.7 g (112 mmole) of N-ethyl-N-[1-oxo-4-[1-[(phenylmethoxy)carbonyl]-4-piperidinyl]butyl]glycine ethyl ester in tetrahydrofuran at ambient temperature is added 200 mL of 1N aqueous sodium hydroxide, and the heterogeneous mixture is stirred vigorously for 1 hour. The reaction mixture is concentrated in vacuo and the residual aqueous mixture is diluted with water and extracted with methyl tert-butyl ether (3×). The aqueous layer is acidified to pH 3 with potassium bisulfate, causing an oil to form. The mixture is extracted with methyl tert-butyl ether (3×). The combined organic layers are washed with brine (2×), dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil is subjected to high vacuum to give N-ethyl-N-[1-oxo-4-[1-[(phenylmethoxy)carbonyl]-4-piperidinyl]butyl]glycine (35.5 g). MS (FAB) 391 (M+H)+.

Provenance & Evidence