Methanol → HCID 54052487, compound

Participants

Reaction Conditions

Reaction Steps

In an inert atmosphere 20 cm3 of methanol are slowly added to a flask containing 1.38 g of benzyl 2-{3-{3-{2-[(2R,4R)-4-tert-butoxycarbonyl-2-(2,3-difluorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}phenyl}propionate (B form), 0.85 g of ammonium formate and 1.38 g of 10% palladium on charcoal. The reaction mixture is heated under reflux for 1 hour, then cooled to a temperature in the vicinity of 25° C. The catalyst is then removed by filtration and the filtrate is concentrated to dryness under reduced pressure at 40° C. The residue obtained is dissolved in 20 cm3 of a 0.1N aqueous sodium hydroxide solution and washed with two times 10 cm3 of diethyl ether. The aqueous phase is brought to a pH of 2 by addition of a 1N aqueous sulphuric acid solution. The precipitated product is separated by filtration, washed with 2 times 10 cm3 of water and dried in air. 1.0 g of 2-{3-{3-{2-[(2R,4R)-4-tert-butoxycarbonyl-2-(2,3-difluorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}phenyl}propionic acid (B form), melting at 130° C., is thus obtained. [α]D20 =+82°±2° (C=0.707%; DMF)

Provenance & Evidence