1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Amino-1-cyclohexyl-3-hydroxy-5-methylhexane

Participants

Reaction Conditions

Reaction Steps

To a solution of Nα -t-butoxycarbonyl-Nα -methyl-Nim -tosyl-L-histidine (195 mg) and (2S,3S)-2-amino-1-cyclohexyl-3-hydroxy-5-methylhexane (82 mg) in dry methylene chloride (10 ml) which was cooled at 0° C., was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (72 mg). The mixture was stirred at 0° C. for 3 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (20 ml) and the solution was washed with 10% citric acid solution, saturated sodium bicarbonate solution, and water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:n-hexane, 2:3, V/V, as eluent) to give (2S,3S)-2-(Nα -t-butoxycarbonyl-Nα -methyl-Nim -tosyl-L-histidyl)amino-1-cyclohexyl-3-hydroxy-5-methylhexane (166 mg) as an amorphous powder. Rf: 0.29 (ethyl acetate:n-hexane, 3:2, V/V)

Provenance & Evidence