Hydrochloric Acid → alpha-(4-(N-methylcarbamyl)aminosulfonyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetic acid

Participants

Reaction Steps

To a stirred solution of 570 mg (1.23 mmol) of the product of Step A in 6 mL of methanol was added 540 μL (2.71 mmol) of 5N sodium hydroxide. The reaction mixture was allowed to stir overnight after which TLC analysis (90:10:1 chloroform/methanol/acetic acid) indicated the saponification had proceeded to completion. The reaction mixture was acidified to pH=2 using 6N HCl, poured into water, and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered and evaporated in vacuo to give the crude product. Purification of the crude product by silica-gel flash chromatography using (92:7:1 chloroform/methanol/acetic acid) afforded 384 mg (70%) of the title compound as an amorphous solid.

Provenance & Evidence