Citric Acid → HCID 54186349, compound

Participants

Reaction Steps

Under ice-cooling, trifluoroacetic acid (1.2 ml) was added to a mixture of tert-butyl 2-[3-[2-(4-tert-butyl-2-thiazolyl)ethoxy]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (185 mg, 0.25 mmol) and dichloromethane (2 ml), and the resulting reaction solution was stirred at room temperature for 3 hours and then concentrated under reduced pressure. Saturated sodium bicarbonate aqueous solution was added to the resulting residue and the product formed was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in water, and the solution obtained was adjusted to pH 2 by adding 10% citric acid aqueous solution. Thereafter, the solid material formed was collected by filtration and purified by silica gel column chromatography (eluent=chloroform:methanol=50:1) to give 2-[3-[2-(4-tert-butyl-2-thiazolyl)ethoxy]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid 0.5 hydrate (58 mg, 0.086 mmol, 34%).

Provenance & Evidence