Chloroform → N-(4-iso-propylbenzenesulfonyl)-alpha-(4-cyanomethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of the crude product of Step A dissolved in 1.5 mL of methyl sulfoxide was added 0.050 g (0.762 mmol) of potassium cyanide at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 1 h when TLC analysis (80:15:1 CHCl3 --MeOH--NH4OH) indicated that the reaction was complete. The reaction mixture was diluted with EtOAc and 10% aqueous NaHSO4 solution. The aqueous phase was separated and the EtOAc portion was washed with brine (2×10 mL). The EtOAc portion was then dried over MgSO4, filtered, evaporated to a residue, and purified. Purification was done by reversed phase HPLC (Waters Millipore Delta Prep 4000 with Delta-Pak C18 15 μm 100 A column cartridge) with a solvent system of 30:70 water-acetonitrile and 0.1% TFA buffer. The purified fractions collected were combined in a round bottom flask, frozen in a -78° C. dry ice-acetone bath, and lyophilized. The resulting lyophilized powder afforded 0.071 g (35% 2-step yield).

Provenance & Evidence