Dicyclohexylcarbodiimide → 5-Hydroxy-N-[S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteinyl]pentylamine

Participants

Reaction Steps

To a stirred solution of S-benzyl-N-(3-benzylthio-2,2-dimethyl-propionyl)-L-cysteine (4.18 g) and N-hydroxysuccinimide (1.15 g) in DMF (10 ml), DCC (2.06 g) dissolved in DMF (10 ml) was added dropwise under ice cooling and the mixture was stood overnight. The mixture was filtered and 5-aminopentanol (1.55 g) dissolved in DMF (30 ml) was added to the filtrate. The mixture was stirred for 3 hr. at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. Ethyl acetate layer was washed with saturated sodium bicarbonate solution, water and then saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 3.4 g (69%) of the titled compound.

Provenance & Evidence