Methanol → HCID 9957833, compound

Participants

Reaction Conditions

Reaction Steps

30 cm3 of methanol are added slowly under an inert atmosphere into a round-bottomed flask containing 2.0 g of benzyl (4R) -3-{3- [2- (4-tert-butoxycarbonyl-2-cyclohexyl-3-thiazolidinyl)-2-oxoethyl]-ureido}phenyl-acetate (isomer A), 1.7 g of ammonium formate and 2.0 g of palladium on charcoal (10% Pd). The reaction medium is heated to reflux for 2 hours and then cooled to a temperature in the region of 25° C. The catalyst is separated by filtration and the filtrate is concentrated to dryness under reduced pressure at 40° C. The residue obtained is dissolved in 25 cm3 of 0.1N aqueous sodium hydroxide solution and washed with twice 10 cm3 of diethyl ether. The aqueous phase is brought to pH 2 by adding 1N aqueous sulphuric acid solution. The precipitated product is separated by filtration, washed with twice 10 cm3 of water and dried in the air. 1.0 g of (4R) -3-{3- [2- (4-tert-butoxycarbonyl-2-cyclohexyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenylacetic acid (isomer A), melting point 115° C., is thereby obtained; [α]D25 =-32.9°±1.2° (C %=1.2; DMF).

Provenance & Evidence