2-Methylbenzenesulfonamide → HCID 53883197, compound

Participants

Reaction Steps

To a mixture of 4-[7-(cyclopentylacetamido)naphth-1-ylmethyl]-3-methoxybenzoic acid (375 mg), 2-methylbenzenesulfonamide (231 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (259 mg) in methylene chloride (9 ml) was added 4-dimethylamino pyridine (165 mg); and the mixture was stirred for 24 h. The mixture was added to 60 ml of 1:9 tetrahydrofuran:ethyl acetate: and the organic solution was washed (1N HCl, water, brine), dried (MgSO4), and evaporated. The residue was purified by flash chromatorgraphy, eluting methylene chloride:acetone:methanol (90:8:0, 90:8:1, 90:8:2 successively). The crude product was recrystallized from 2:8 methanol:methylene chloride and petroleum ether to give the title compound as a colorless solid (263 mg, 51%); mp 248.0°-249.0° C.

Provenance & Evidence