Sodium Hydroxide → HCID 178488038, compound

Participants

Reaction Steps

A solution of methyl {4-[(5-methoxy-2{[4-methoxy,3,5-dimethyl(2-pyridyl)methyl]sulfinyl}benzimidazolyl)sulfonyl]-3,5-dimethylphenoxy}acetate (Intermediate A6, 2.96 g, 0.493 mol) in 250 mL of dimethoxyethane was stirred rapidly as 49 mL of 0.100 N aqueous sodium hydroxide was added. The mixture was concentrated at aspirator pressure (bath temperature<22° C.). The residue was reconcentrated from 200 mL of dimethoxyethane, left briefly at high vacuum, and partitioned between ethyl acetate and water. The aqueous layer was washed with several portions of ethyl acetate and was then concentrated at high vacuum. The residue was partitioned between ethyl acetate and water at pH 3. The aqueous layer was extracted with an additional portion of ethyl acetate, and the combined organic layers were reduced in volume and diluted with hexanes. The resulting solid was collected and combined with a second crop recovered from the filtrate. This material was washed with 10:1 diethyl ether:tetrahydrofuran, dissolved in dimethoxyethane, neutralized with 0.0100 N sodium hydroxide, and washed with ethyl acetate. The product, title compound weighed 0.925 g (31%).

Provenance & Evidence