1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl(1r)-2,2-dimethyl-1-((4-((5-methyl-3-oxo-1h-imidazo[1,5-c]imidazol-2(3h)-yl)methyl)-1-piperidinyl)carbonyl)propylcarbamate

To a solution of Boc-D-tert-leucine (0.69 g), HOBt (0.69 g) and WSC (0.86 g) in acetonitrile (20 ml) was added a solution of 5-methyl-2-(4-piperidinylmethyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.91 g) as described above, DBU (0.6 ml) and triethylamine (0.61 ml) in acetonitrile (20 ml), and mixed for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in dichloromethane. The dichloromethane solution was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate/methanol=10/1) to obtain the title compound as colorless powder (1.2 g, 66%).

1. additionmixed for 15 hours
2. distillationThe solvent was distilled off under reduced pressure
3. dissolutionthe residue was dissolved in dichloromethane
4. washThe dichloromethane solution was washed with an aqueous sodium hydrogen carbonate solution
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customthe residue was purified with basic silica gel column (ethyl acetate/methanol=10/1)

ORD record

ord-6a82fc3ea4064785ba3fd6ad8fdb3702

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820673B2