1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane

Participants

Reaction Steps

To a solution of Nα -t-butoxycarbonyl-Nα -methyl-Nim -tosyl-L-histidine (2.77 g) and 2(S)-amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (1.49 g) in dry methylene chloride (60 ml) which was cooled at 0° C., was added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (1.25 g). The mixture was stirred at ambient temperature for 3 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (200 ml) and the solution was washed with 0.5% hydrochloric acid, saturated sodium bicarbonate solution and water successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (1% methanol in chloroform as eluent) to give 2(S)-(Nα -t-butoxycarbonyl-Nα -methyl-Nim -tosyl-L-histidyl)amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (1.61 g) as an amorphous powder.

Provenance & Evidence