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

Temperature

0 °C

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)

1. customAfter evaporation of the solvent
2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
3. washthe solution was washed with 10% citric acid solution, saturated sodium bicarbonate solution, and water
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified with silica gel column chromatography (ethyl acetate:n-hexane, 2:3, V/V, as eluent)

ORD record

ord-42f6e92d63ca42ab88bbc5ba853269c6

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05491132