Hydrochloric Acid → Methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of methyl 2-benzamido-2-(3-methoxy-6-methyl-4-trifluoromethylsulphonylphenyl)acetate (0.3 g, 0.65 mmol) triethylamine (0.16 g, 1.6 mmol), palladium acetate (5 mg, 0.022 mmol) and 1,3-diphenylphosphinopropane (9 mg, 0.022 mmol) in dimethyformamide (3 ml) and methanol was saturated with carbon monoxide gas using a bubbler and then heated to 70° C. for 3 hours and overnight at room temperature under an atmosphere of carbon monoxide using a gas filled balloon. The mixture was acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (2×). The combined extracts were washed with a saturated solution of ammonium chloride, dried, filtered and evaporated to a solid. Chromatography on flash silica eluting with diethyl ether-hexane (3:2, 4:1) gave methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate as a white solid.

Provenance & Evidence